Onboarding New Team Members

Many times I get to kick off a project with a team that has worked together before.  This certainly has its advantages…. Everyone generally knows how everyone else will act and work with the group.

Other times, though, I've had team members join mid-project.  This could be due to someone leaving the company, being out of office or needing more resources to get the job done.  Regardless of why, this new joiner can disrupt the team in several ways - they may communicate differently, they don't know the norms and they have to build relationships up from nothing.

Ensuring the new person feels welcome and meshes with the group is critical to its success.  Frequently I see this process being ignored or sped up in the name of 'get the job done'.  I find that while this approach may get them doing work more quickly, it doesn't result in an optimal outcome.  Sure, they're working, but they’re also lacking connection with their team.  They're less effective because they don't know where to go for some things, and because they don't know how to really work with everyone else.

I've found a few things can help get someone new onboarded and success :

• Make sure they meet everyone - this sounds simple, but make sure your new team member has time to connect with everyone else on the team.  I've found that prepping them beforehand with some background can also help guide the conversation (e.g. Sally has a background in coding, she's a great resource for X).

• Get time with them early - don't wait until they've already finished their first week!   Meet with them early and often, this both helps demonstrate that you care about them and their success, but also ensures they have time to get a feeling for how you operate.

• Proper resourcing - make sure they have whatever access they need to do their job as soon as they join.  Nothing saps morale faster then not being able to v successfully because your account isn't live.

• Ask them how you can improve - this new member will bring in new experience and knowledge that can help your team.  Asking them for their input on what the group can do better both shows you care about their thoughts, but also helps them buy into the group.

It does take time and effort to integrate new folks to the team.  That time is more than well spent - not only will the team benefit from their skills and time, they'll benefit from being part of the team.

Ownership

Lots of work is done in projects to determine things like who is accountable or responsible for various items.  This is a great necessary step, but I find many times we stop there.  We write down our RACI, all agree on it and then move on.  Agreeing on these things is important, but it doesn’t necessarily translate to anyone feeling ownership of the project (or pieces of it).

Ownership extends beyond taking on some work.  It extends deeper, into feeling that you truly own it.  It’s yours, and how you handle it is a direct representation of yourself.  Frequently this feeling of ownership is lacking in projects, which leads to some less than desirable outcomes:

• Lack of “push” - When someone doesn’t feel ownership of a particular item, they won’t push to complete it the same was as if they do feel ownership.  They won’t go that extra mile, as that extra question, or do that extra test to really make it work.

• General lack of interest - If someone doesn’t feel like they own a task or item, they won’t be as interested in it.  This shows up as individuals not being as curious about their work and not understanding it as well as if they did feel ownership.

The good news is that ownership is something that can be cultivated.  Some individuals will have more or less levels of it, but it can always be improved.  There’s a few things that can help an individual build a sense of ownership, including:

• Demonstrating ownership - It can be hard to feel ownership if you don’t see others practicing it.  In order to help others build their sense of ownership, YOU have to actively demonstrate it.  Showing your interest in the topic, constantly knowing what’s going on with it and generally moving it forward will help others cultivate their sense of ownership.

• Getting to the core - Individuals may have some reason they don’t demonstrate ownership, one they may not even be fully aware of.  Having a direct conversation with them about ownership, and why they aren’t demonstrating it, can help them flip the script.  

• Staying on them - A more intense/extreme tactic is to constantly ask them how their task is doing.  Do they know the status?  Why it’s important? Who’s impacted?  Consistently pushing them for info and being present will force them to internalize a sense of ownership, if only to be ready for you.

You work, I work

I’ve spent a lot of my career on various project teams.  I’ve been on large, multi-national deployments, handled startups getting their medical benefits for the first time, run projects entirely on my own and been part of much much larger teams.  While they were all very different, to me they all had one thing in common; the project team.

Teams were obviously composed of different people at different times and places, but all projects have some kind of team.  How that team functions is critical to the success of the project; a dysfunctioning team increases the risk of the project going poorly.  This isn’t to say a perfect team will always have a successful project, but a dysfunctional one will be at a much higher risk of failure.  

As the project manager (or really any non-SME / technical role) I tended to be close to the work, but not close enough to do a lot of it.  At times, I also have to be the one to decide if the team needs to work late or work over a weekend or a holiday.  Over time I’ve always followed a very important rule when I make those decisions ; if anyone on my team has to work extra hours, I will be right there with them.

Essentially this means that if any of my team is working a weekend (or over time) so am I.  At the very least I’m in the office with them (or online and on slack) to simply be around them.  This is incredibly important because it shifts the dynamic from “I’m telling you to give up spare time to work” to “we’re in this together to get it done”.  I’ve found this not only helps break down push-back to working extra, but it can help inspire others to volunteer to pitch in as well.

I also find this a great way to build space for myself to take on tasks I “don’t have time to do” otherwise.  This time is focused on the project my team is doing, but can be used to catch up on other aspects like improving documenting, reviewing lessons learned and updating plans.  For me, it all boils down to the team aspect of a project team.  We’re all in this together.

Let others do their jobs

I’ve had many transitions in my career; points in time where my job shifts a bit and I now get to do something new.  Doing something new also generally means no longer doing something old though, and this can be tough.  Tough, because you’re used to doing it.  Tough, because everyone knows YOU do it.  Tough, because you don’t think someone else can.

Letting go of those things is hard, but it’s also important to our own development, and maybe more importantly, for others to develop.  If we never let go of the things we used to do, the things that we’ve grown out of, we’re essentially cheating others out of the same opportunity we had to learn those skills.  If we step in and keep doing the same work we used to do, not only are we spending our time in an area that won’t help us grow, we deny others their chance to grow.

I’m not saying we don’t help someone who’s taken over an old role.  We certainly need to help set them up for success by giving them support, teaching them the ropes etc.  What we want to be careful of, however, is continuing to do that job even after we’ve moved on.  In addition to preventing them from learning, we also distract ourselves from our new role.  There’s only so much time, and any minute spent on the old role is one less spent on the new one.

I see this frequently happen when a new ticketing system and team comes online.  The group that used to do the work doesn’t want to let go.  They’re concerned the new system won’t track everything, or that the new team won’t be up to snuff.  There’s almost always SOME amount of disconnect as the new team comes online, but those aren’t just negative experiences.  They’re also opportunities for the new team to learn how to improve.  Making mistakes is one of the best ways to learn, and allowing others to make them is beneficial in the long term.

I’ve found that focusing on the new work, and checking in regularly with my replacement, is a great balance between the two.  This allows me to excel in my new area, but also keeps a communication channel open in case something is needed.  This helps build a strong relationship that makes the transfer more seamless, and easier, than if I stayed entirely involved.

The Utility of Feedback

We rely constantly on feedback in our lives.  Our bodies give us feedback on how it’s doing (hungry? Tired? Both useful pieces of feedback).  When we play a game we’re reliant on feedback on how we’re doing.  Social interactions with our friends and family give us feedback on how well (or poorly!) our jokes land.  All of this feedback is good, it helps us take care of ourselves, get better at games and tell better jokes.  Feedback at work, however, usually feels like a negative thing.

This to me is incredibly odd.  Many of us spend the majority of our waking time at work, so I would expect work-related feedback to be treated at a premium.  Frequently though, it’s seen as negative.  I’ve written previously about “having” to give feedback and the negative connotation around that phrase, but it goes beyond just “having” to give it.  Many of us are also reluctant to seek out, or even accept, feedback.  Giving feedback is also something we shy away from, after all, it’s very hard to first identify something someone can improve on (or where they’re doing well) and then communicate that to them.

Regardless of our reluctance, however, feedback requires two things to be effective.  It must be timely, and specific.

Timeliness

Imagine someone you trust comes up to you and says something like “hey, during that meeting four months ago you did a great job presenting X topic, it could be even better by also doing Y”.  This is useful, since it’s specific… but it’s made less useful since it’s months later.  You may not really remember that presentation or topic.  You may have already improved that skill so this feedback isn’t as useful.

Ideally feedback is provided as soon as possible.  I’m not saying interrupt a meeting, or call someone at 2am, but the sooner feedback is provided, the more useful it is to the recipient.  Not only does it makes it easier for them to apply it, it’s also still fresh in their minds.  They know the context, and they know how it can be applied.  Waiting to give it robs the recipient of a lot of the utility.

Specific

Imagine someone you trust comes up to you and say something like “hey, I checked out that paper your wrote yesterday and noticed some grammar errors you made”.  This is useful since it’s timely (they’ve told you close to the event), but it’s made less useful by not being specific.  Sure they mentioned grammar errors… but WHAT errors?  Are you mis-using commas?  Not using conjunctions?  Adding too many spaces after periods?  Without the specific information this feedback is not very useful.

Making feedback specific helps the recipient by clearly showing what they’re doing that can be improved.  Ideally specific examples can be pointed out and used to exemplify where improvements can be made.  THis makes it considerably easier for the recipient since they clearly see what they’re doing that needs improvement.  Being vague (regardless of the reason) robs the recipient of a LOT of the utility of feedback.

Wrap Up

Most people most of the time want to improve something, and feedback is one of the best tools to do that.  Like any tool, however, it needs to be used properly.  Being timely and specific gives the recipient the best chance of using the feedback effectively.  Not only does it illustrate exactly what needs to be improved, but it’s provided close to the event itself making it much easier to translate into reality.

We’re human first

Working in tech I’ve found it very easy to forget that the human element is still there.  It’s REALLY easy to focus on how the systems interconnect, or which technology you’re using, or what error popped up… but it’s far more important to remember that everyone involved, the people using and complaining and working the tech, are human.  That said, I imagine that many folks who work in tech don’t do it because they want to interact with folks, instead they do it because tech is amazing.

This split can make things…. Problematic.  Think back to any interaction you’ve had with someone on a support team who’s been less than empathetic.  Or hasn’t taken the time to get to know you… or cannot pronounce your name properly (or even cares).  They may do a great job of fixing whatever problem you have, but the interaction still left a bad taste in your mouth.

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Remembering that we’re all human also goes both ways.  The customer asking for help should keep in mind that tech may have had to work overtime to fix a problem and really just wants to relax.  That stakeholder who’s upset their deliverable will be a bit late needs to keep in mind that the project team is doing everything they can to help.  That same help desk technician, however, needs to remember that the person calling in to get help for the same problem they’ve fixed 9123 times today still needs their help.

It can be incredibly hard to remember this basic rule, especially when things go sideways and the pressure is on.  We’ll find ourselves falling back to demanding things, placing blame, and other behaviors that “feel good” because we’re able to vent, or we think we’re doing something that helps… when really it just signals we don’t see others as being people.  Instead, this behavior signals we see others as not needing our empathy or compassion.

There’s a few tricks I’ve found that help keep the “we’re all human” aspects near the top:

• Small Talk - While it seems like it’s just a time waster, small talk (how was your weekend, what’s up with those boxing gloves in your background, etc) help uncover small pieces of folks.  This, in turn, helps make them less “This person is wasting my time” and more human.

• Asking them for help - This is very useful if they don’t think you’re as human as you’d like.  Asking them to help out with something, even something small, helps them see you as another person and not just a machine that pushes buttons.

• Checking in - I’ll randomly reach out to folks I haven’t worked with in a while just to say hello, or to share an article I think they’ll like.  This both helps keep our relationship going, but also shows them I’m interested in them beyond just the project we’re on. Some of my stronger relationships have come from this approach.

Dealing with crappy weeks

We've all had a crummy day or week.  You know those times when everything seems to go wrong and any bit of news is bad news?  That week when a major deployment you’re managing hits a massive (or even small) snag?  They hit all of us differently, from shrugging and moving on, to getting worked up emotionally, to taking it entirely personally.  For most of us they’re not fun (especially if you feel like you’re responsible for the problem!), but there are ways to help get through them.

Separate the emotion

Emotions are great tools in many situations, but when we’re evaluating a problem they can get in the way.   At the very least the emotions of "I screwed up", "I hate I have to XYZ" and others suck up mental bandwidth we should be applying to solving the issue.  At worst they end up catching us in an endless cycle of "I'm terrible, I can't do anything".

The first step is to simply acknowledge that your emotions are getting the way.  This is easier said than done, but feelings of anxiety are generally a good indication that emotion may be clouding things.  Taking time to write down how you’re feeling can also help clear out, or at least minimize emotional responses.  Having a friend or colleague at work you feel comfortable talking to is also incredibly helpful.  They can both help you identify what the actual problem is and figure out good steps forward.

Keep moving and find the positive

During a crummy day/week finding small wins, or even making tiny amounts of progress, can help turn things around.  Finding these wins gives you an anchor, something to point at and say “yeah, it’s not so bad”.  These moments can also help improve your emotional state, helping to dig yourself out of that hole as well.

I find it easiest to review the current work I have and seeing what low-hanging fruit exists.  There’s almost always something you can pick off in 15-30 minutes that will move the needle.  Maybe it's something “too small” to do normally, or something that is a passion project.  In this case it doesn’t really matter WHAT it is, just that it is something you can accomplish and feel good about.

Make a Connection

Talking through the crumminess can also be a big help.  Ideally there’s someone at your workplace that you can speak with and just go over what happened.  At the very least they can be a sounding board for you to just get everything out.  More likely they can offer some insight into what’s going on, possible steps forward and the like.

Speaking to folks outside the office can also help, although they may not be able to offer the same insight as a colleague (if only because they don’t work with you).  This, however, can be an advantage; they’re not also in the same situation and have a different perspective.  At the very least you can unload a bit with someone you trust.

"I had to give" someone feedback

Feedback is critical to learning.  Without understanding the impact our actions make we cannot course correct and become better.  One of the best sources of feedback is our team; the folks we work with.  Not only do they have an understanding of how we work, they understand something about the work itself. This gives them insight into how we can improve in specific areas, as opposed to generalities.

Understanding that feedback is important is one thing, but being able to accept it is something else entirely.  Many times the phrase “I had to give so-and-so feedback” is used when describing giving feedback.  This phrasing sets up a bit of an adversarial understanding.  They’re giving feedback because they “have to”, because something went wrong that needs to be fixed.

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Phrasing

This phrasing instantly tells everyone that someone screwed up.  It tells the team that so-and-so made a mistake and the boss (or whomever) has to come down from on high to make sure it doesn’t happen again.  This phrasing also puts the boss into the mindset of “correcting a bad thing” instead of “helping someone improve”.  At this point it stops being positive feedback, and instead turns into something closer to a punishment.

The person receiving the feedback will also pick up on this difference.  Going into a meeting where you “have to be given” feedback primes you for being in a defensive / negative headspace.  It takes what should be a positive event - learning to become better - and shifts it into a negative event - being dressed down.  While this certainly isn’t guaranteed - after all everyone will accept and interpret feedback differently - it certainly doesn’t help.

Part of how feedback is delivered is built into the culture of the company - do folks expect regular, honest discussions on how they’re doing and where they can do better? - or do they expect to only be told when they screwed something up?  While this framework will certainly impact any feedback discussion there’s a lot a team, or even an individual, can do to frame feedback as a positive.

Use different words

As noted above “I have to give feedback” sounds negative, so just say something different.  

• “I liked XYZ you did, let’s talk about how you can get even better next time”.

• “I’ve got some ideas on how you can increase your impact”

The intention is to present the discussion as a positive, “lets help you do even better” talk vs a “you screwed up, don’t do it again” talk.  The words you use to transmit that intention are incredibly important… take time to think up a way to indicate you’ve found something they can do better, without sounding like a demerit.

Openly talk about feedback

Many times feedback is only provided during set times (generally around performance discussions).  This not only guarantees it’s stale (ever had a manager bring up something that happened 4 months ago? Or not bring up anything at all?), it also clearly ties it to performance.  This linkage is dangerous since it puts everyone in the mindset of “feedback had better be positive or I won’t get my bonus/increase/whatever”.

This also makes feedback a rarity, something that only happens at set points.  This breaks any positive habits around feedback and instead sends you scrambling to look up what feedback is, how to write it and how to accept it.  Knowing that it’s coming up, and that you and your team don’t regularly do it, just adds to the stress of it all.

Many of these challenges can be overcome by making feedback a regular, and open, thing on your team.  The more the team experiences feedback, the more the team talks about the feedback and the more open it is will make it easier to give, and accept.

Speaking up when you find something

If we’re really lucky on projects nothing will ever go wrong.  Many of us, however, never get that lucky… Instead, we find ourselves looking at an issue or a challenge that blocks our project.  Many times when this happens we shrug to ourselves and start trying to figure out a solution.  This approach may result in us solving the challenge, however, it has a lot of problems.

Ideally when we find a problem we take a few steps before we start trying to solve it.  These steps help ensure that we can solve the problem while minimize risk.

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Let other folks know

As soon as we’re aware of a problem we should let other people know.  While the exact folks we alert may differ based on the project we’re working on, our company culture and some other factors, we still need to reach out.  I default to telling my immediate manager and anyone else working on the project, but other stakeholders may be included as well.  This helps prevent them from being caught unawares, either by finding it on their own, or by having someone else tell them about it.

This also sets us up to get help in case we need it.  While the problem may seem to be something we can handle at first blush, it’s always possible it will be something we can’t.  While we can certainly ask for help after something has blown up, it’s easier to ask for help before things get too crazy.

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Share information

Letting others know that something broke is the first step, but we also need to be proactively sharing what we’ve discovered.  Initially this may be a short message along the lines of “I found XYZ error code in the system”, but as we go we need to keep sharing information.  Providing regular updates has many of the same advantages as just letting others know; they won’t be surprised when someone else talks to them and they’ll be able to help.

This approach also lets us divvy up work, for example you can have other team members handle communicating with stakeholders while you handle the fix.  Sharing information, especially with stakeholders, is also important to keep them calm.  It’s highly likely that stakeholders don’t understand the technical ins and outs and just know “it doesn’t work”.  Sending out regular updates helps maintain your relationship and makes them feel connected.

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Keep Sharing Info

As you go through the process of fixing the challenge, keep sharing information.  It’s really hard to provide TOO much info when something breaks.  Continually updating throughout the life of the problem means no one is unaware of your progress, or if you need other resources for help.

On Proactivity

IT does a ton of work to support a company.  We make sure billing systems accurately charge clients.  We make sure our HR systems pay everyone properly, and we make sure our websites are up and accurate.  All of these things are incredibly complex challenges that require a great deal of expertise and skills to manage successfully.  Despite of all this work, however, IT is generally perceived as a reactive function; we just sit around waiting until someone reports a problem to us.

Certainly some part of our function is reactive… we do, after all, have a help desk and support portal to solicit tickets.  There will always be some portion of our work that is reactive, we cannot, after all, be everywhere at once.  There will always be SOME challenge that pops up in an area we don’t have eyes on.  Just because a small percentage of our work necessitates reactivity, we shouldn’t accept only being reactive.. Indeed, there is a LOT to gain from doing the opposite, from being proactive.

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Being proactive means a number of different things in tech.  Most importantly it means letting others know that something is going on.  Being in IT means we get an advanced view of how the systems are operating.  We get dashboards, alerts and reports that most folks don’t get… and even if they DID get them they wouldn’t necessarily understand what they mean.  This makes proactive communication the single most important thing we can do to increase out impact.

I take this lesson to heart and make alerting folks one of the first things I do when I find a problem.  (The only step I would take before this would be to stop the immediate bleeding to help minimize the impact of the problem).  This have a number of advantages:

• Get ahead of the problem - Letting folks know about a problem before they find it helps prevent the wave of “OMG XYZ thing broke, help!” emails/calls/slacks/visits/telepathic messages that will come once folks realize there’s a problem.  Your email just saved god knows how many tickets.

• Builds partnerships - This is an important one!  By showing your partners that you’re actively watching out for them you build trust.

• Rallies the troops - Proactive alerts also let’s your team know that somethings happening.  This gets more eyes on the problem, and helps solve the challenge more quickly.  It can also help tap into other teams sooner since they’re now aware of the issue.

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The good news about being proactive is it doesn’t take much effort… a few sentences describing what you discovered and that you’re looking into it goes a LONG way to avoiding an escalation.

Owning Mistakes

Mistakes… we all make them (citation needed), but not many of us are comfortable talking about them (or even sometimes acknowledging they happen).  I find this lack of comfort to be a very interesting cultural outcome, since discouraging talking about mistakes means we’ll be making more.  Even worse, it means the ones that do occur will end up hurting us more.

I recently had a great discussion with a colleague about how we can get more comfortable sharing mistakes (this is a fascinating topic that I’ll touch on in another post).  In essence they were asking how we can go from a state of being fearful of owning mistakes and exposing ourselves to retribution to a state of feeling OK pointing out when I screw up.  Their fear was centered around what would happen at our next performance review since we’d essentially be feeding our managers ammo on where we failed.  While I completely understand this mindset (it’s one I imagine many of us have experienced… the manager who sees a mistake as something to hammer down on vs. an opportunity to improve), it’s one that I do not ascribe to for a few reasons.

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Everyone makes mistakes

It’s a simple fact of our reality that everyone makes a mistake at some point (or several…).  Trying to ignore this fact is essentially lying to ourselves… after all, we know that at SOME point we’ll make a mistake... and that our boss will make a mistake… and that everyone else will too.  Since we know it’s going to happen, we don’t gain anything by hiding it.  The best possible outcome in that scenario is no one finds out… worst case is someone does; in this case instead of asking how they can help fix it they’ll ask why you hid it.

You could also think of it this way - your manager knows at some point you’ll make a mistake. By exposing them, instead of letting your manager find them, you show that you can be trusted, that you recognize when you need help.  This not only helps strengthen the relationship with your manager (see the third point), but also gets you in control of the conversation.  Proactively bringing it up lets you frame the discussion as a “I made a mistake and want to avoid doing it again” instead of a “You really screwed up”.

Owning our mistakes gives us strength

Hear me out on this one.

The default assumption in many places is that individuals will not call out their own mistakes (despite everyone knowing mistakes are made).  After all, it REALLY doesn’t feel good to stand up and say “I made a mistake”.  Our ego (that voice inside that pumps us up/tells us how awesome we are/etc) is threatened by this, so we avoid that internal pain by not saying anything.  This easy way out protects us in the short term, but can come back to bite us when the mistake is caught later.

Actively calling out our mistakes demonstrates to others that we’re aware of where we need help and where we can grow.  It tells others that we’re human too, and that even us as the XYZ expert can stumble.  By bringing your mistake into the open you not only make it easier to get help, you also make it easier for others to share their mistakes.  This not only enables your growth by allowing others to help you improve, but strengthens the entire team by sharing those lessons.

Owning our mistakes builds relationships

One of the biggest advantages in admitting to our mistakes is the boost it gives our various relationships.  As noted above, they also make mistakes, so knowing you’re comfortable sharing yours will make them feel better about working with you.

Being proactive and calling out when we’ve made a mistake lets our partners know we’re serious about helping them… after all, we could have just let is slide.  Now this isn’t to say I just call up someone and say “Hey, I crashed the server, good luck”.  Instead I’ll first figure out how to undo (or at least mitigate) the damage.  This further helps my credibility as not only am I proactively alerting them to issues, I’m proactively fixing tem.  This turns what could be a large escalation (imagine a situation where you don’t tell them about the mistake and they find out on their own) into a positive experience.

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Not Easy

I’m not saying any of this is easy… indeed, it can be very challenging to stand up and say “hey, I screwed something up”.  The benefits, however, outweigh that short-term discomfort.  The good news, though, is that the more we practice this skill, the more we embrace being temporarily uncomfortable, the easier it gets.

Don't play telephone

Do you remember a game called “telephone”?  You know, the one where a group stands in a circle and one person whispers a message into someones the next person’s ear, then they into the next until it gets back to the first person?  The message changes… sometimes folks add in parts on purpose, and sometimes they just mis-understand what they were told.  The end result, however, is the message changes in (hopefully funny!) way.

In the game, that’s the point!  It’s fun to see what happens when multiple people are in the middle since you never really know what will come out the other side.  When you’re at work, however, this communication drift causes a LOT of problems.  This lesson will go over how to identify when you’re in a game of telephone and how to constructively resolve it.

There’s three things you want to do in these situations:

1. Get in direct contact with the person impacted

2. Let the reporter know you’re reaching out the impacted person 

3. Educate both parties on what to do in the future

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Step #1 - Connect

Getting in direct contact with the person impacted can be harder than it seems, as sometimes there is more than one person between you and them.  Frequently I see 2, 3 or sometimes more people in the chain, all “helpfully” passing along a message to someone else.  Unfortunately, as our game showed us, each node in communication introduces a chance for an error to be introduced, and the drift from the original message only increases each time it’s passed along.  To help with this, the first question I ask myself when I get a new request, whether it’s an email, instant message or ticket, is “who is this REALLY coming from?”.  For example, if one of my data analytics partners sends in a request to get a new team member setup with access, that new team member is really the person how needs help.  In that case, I’d connect directly with them to understand their needs, versus the perceived needs that are being reported.

Frequently the folks in the middle also don’t fully understand the request; they are, after all, filtering it through their own experience and ideas.  This can result in your understanding of what needs to be done being drastically different from what is needed.  Identifying, and connecting directly with, the originator of the request helps mitigate this risk substantially.

Step #2 - Update

Once I think I’ve identified the person impacted, I’ll connect to them directly, and also let the reporter know what I”m up to.  That second bit is critical; if they are unaware I’m helping they’ll keep coming after me.  Some quick examples:

• If it’s an email - I’ll move the reporter to CC or BCC and email the impacted person directly.

• If it’s an instant message - I’ll either let the reporter know I’ll be in touch with the impacted person, or get both of them in a group message

• If it’s in person - Similarly to an instant message I’ll let the reporter know what I’m up to, then connect with the impact person directly.

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Step #3 - Educate

Keep in mind the reporter is just trying to help their colleague out, they’re not intentionally making things harder for you.  This makes these situations great learning opportunities.  As part of your communication, you can let the reporter know how these situations ideally should be handled.  While the exact approach will differ by organization, I prefer for the person impact to be the one to report the issue.  Sometimes this isn’t possible, maybe they’re on vacation or unavailable.  That’s totally OK.  In those situations someone else should report it, but clearly indicate they’re passing along a message and include the impacted person on the email, message or thread.  This makes it significantly easier to follow up, and ensures everyone is aware of where they are.

Some examples of language I’ve used:

Example #1

“Hey Tim, thanks for letting me know Rebecca is having login issues.  I’m going to connect with her directly.  I appreciate you forwarding in her request, but please encourage folks to use our help desk (link here), it makes it a lot easier when they reach out directly”.

Example #2

“Hey Tim, Rebecca let me know you’re having problems running your TPS report.  More than happy to help out, but it would be helpful if you report these directly in the future.”

On Perseverance

Perseverance, the ability to keep going despite hardships, is a very important skill to learn, and something I recently had a chance to practice.  On Friday I took what should have been a 4 hour exam… which lasted 5.5+ hours.  Instead of starting this (stressful) exam that I’d spent 8 months preparing for immediately, I was greeted with a black screen and a spinning beach ball.  Despite figuring out how to get help, I ended up waiting on hold for tech support.  For 2.5 hours.  Talking to chat bots. In circles.  At several points I considered just calling it and rescheduling (something that would set me back another two months).  

Instead, I took a moment to breathe and figure out my options… Everything basically amounted to waiting on hold for chat support… or phone support… or chat support again… and again and again.  I figured if I could just get the RIGHT agent on the phone, I’d get in and could take my exam.  It just took my not giving up.  Eventually, 2 hours later I found that agent, and my exam started.  8 questions in it immediately broke.  Again.  This was another chance to give up.  I’d already spent half my allotted time not answering questions, and who knows how much longer it would go on for.  Instead I chose the perseverance route; apply my previous strategy of reaching out again. And again. And again.

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This was not as easy as it sounds. Whatever chat system I was tied into would automatically send me a message “from the agent” every 3 minutes. It was something like “Thanks for your patience, I’m still looking into your issue”, that just repeated. After 40 minutes of non-responses I began asking if anyone was actually there, and they could type in literally ANYTHING other than the stock message to let me know. Eventually I hung up on that chat and opened another, and kept doing that until I found someone who could help me. The same thing happened to me on the phone; after 30+ minutes on hold an agent would pickup, tell me they’d fixed the issue, then hang up. I even asked one to stay on the line until I could confirm the issue was resolved, but they said they couldn’t.

Long story short I ended up passing that exam…. But not after getting a hands-on lesson in perseverance.  In this case it expressed itself in not giving up, in not saying “I give” and quitting, in continuing to look for an answer despite every avenue being non-helpful.  This is hard stuff… it would be SO much easier to just reschedule or do it later, but it wasn’t worth it to me.  Not only would I have to go through all the anxiety of prep AGAIN, all the waiting AGAIN, I’d have wasted almost 3 hours of my life on hold.

Situations like this crop up all the time.  We’re in meetings that we’re bored stupid in.  We have to work on projects that just… never… die.  Something fails and we lose several hours of work that we have to re do.  The challenge is not to get stuck on how annoying/stupid/etc the situation is, but instead of focus on what’s important; being present, completing our work, solving the challenge.

"I" shaped skillsets

Individuals with an “I” shape of skills have one focused their time on delving deep into a single skill.  This means they’ll know everything about a specific tool, concept or area, which tends to make them excellent resources for those topics.  This focus can, however, lead to other skills not being as strong as they could (or should) be.  For example, a technical resource who is incredibly knowledgable about yoru system, but cannot effectively communicate, or a lawyer who knows everything about their area but is incredibly abrasive in interpersonal interactions.

“I” shaped skillsets may not be very common in smaller environments, if only because the level of challenges that crop up on a regular basis don’t necessitate their skills.  Frequently this results in these individuals working as consultants or contractors so they can stay busy.

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The upside of an I

Folks with I shaped skillsets are incredibly important to successfully completing large and complex projects.  This is mainly due to their in-depth understanding of the topic at hand, which tends to allow them to either foresee challenges before they crop up, or deal with them if they do.  While “T” shaped folks or “broken combs” may also possess some amount of skill in those areas, they rarely get to the depth that someone with an “I” shaped skillset can delve.

This means folks with an “I” shaped skill set are great to throw at large, complex problems that fit in their wheelhouse.  Their experience and background will give them a good idea of where to begin tackling the problem, and since they’ve done it all before they’ll know what steps need to be taken and when.  Their innate desire to learn about that topic will also result in them continuing to sharpen their skill set, either through formal training, experimentation or networking with others in their field.  This makes them a great resource for trying new things and getting the most out of their work.

The downside of an I

Given the immense amount of time and focus it takes to develop a single set of skills this deeply, “I” shaped skillsets tend to leave folks lacking in some areas.  When unrecognized this can lead to some severe challenges with projects, as this individual will keep chugging along their path without realizing other areas may need attention.  For example, understanding the need to communicate changes to a project’s scope is incredibly important, however, if I’m entirely focused on a technical buildout I may not share that information in time.

The extreme depth of skillset an “I” shape offers also can make it hard to find one.  This is less a challenge for that person, and more for someone seeking those skills.  This can lead to increased market demand, as well as scarcity (think back to how hard it can be to find an expert in some smaller fields).  The focus on one particular area may also blind this individual to learning about other areas, potentially leading to not fully understanding how their work interacts.

Managing an “I”

Managing an I

The best advice I can provide here is to learn to identify when someone has an “I” shaped skill set and where that skillset ends.  Theres a number of signs that will help indicate an “I” shaped skillset:

• Long history with one technology, concept, etc. - Individuals who have specialized over a number of years in one field may tend to be “I” shaped.

• Disinterest in other areas - Not expressing interest in other disciplines, ideas, etc. while focusing entirely on one is also a good indication.

Knowing where these edges are allows you to find ways to support them, whether it be through integrating them with a team of “T” or “broken combs” to help fill out the gaps, or someone skilled in managing “I” shapes.  You can also look for groups of “I” shapes and have them work together.  This can result in multiple folks with deep skill sets playing off each other and performing great work… you just need to be careful they all aren’t blind to each others areas.

Being direct, and repetitive, with communication can help avoid potential problems as well as folks in the “I” shaped bucket sometimes end up assuming others will fill in the gaps, or simply forget to take specific actions (e.g. communicating updates).  Consistently connecting with them (or putting them on a team that’s stronger in those areas) can help maximize their impact.  Helping ensure their schedules are cleared can also be helpful as it allows these folks to focus their time.

If you’re an “I”

Similar to someone managing an “I” the best thing you can do is to be aware of where your skill sets end.  Knowing this boundary will help you work with a team (since you can call out where someone else needs to step in), and where you can choose to improve.  Knowing the depth of your skill is also important, as many folks will turn to you for all the answers about a specific area.  While you may be a super-expert, there’s always *something* you don’t know… and know that edge is just as important and knowing everything else.

Asking for feedback on how to improve your overall performance is also a great (if not uncomfortable) idea.  There’s no expectation that you master other areas or take on more work, but there may be some simple and straight forward things you can do to help keep things running.

On trees

Details are important, it’s where the devil is (citation needed). Details are what allow a plan to come into focus and and idea to have impact. Without them we cannot fully shape what we’re working on, and can never really be sure we’re done with our task. Despite this, we frequently fail to fully understand the details on what we do. We embark on tasks without taking the time to fully examine the minutia that defines our work. Instead, we focus on the higher-level portions - concepts, ideas - that rely on the detailed work to really stand out.

On one hand I can completely understand the desire to avoid really getting into the details… it’s tedious.  It can be boring.  It takes time… and there’s SO much of it.  Even what seems to be a “simple” project contains a ton of details when you zoom in.  Asking questions like “who do we talk to about X”, or “what specific steps are needed to complete this task” makes those “simple” projects seem more complex… after all, we started with just installing a new piece of software, why does that have more than one step?

While it is true getting into details can make projects seem to stretch out, the time is more than worth it for a number of reasons.

• Understanding the whole picture - Taking time to understand the details helps flesh out the entire picture you’re looking at.  It’s similar to looking at a painting and noticing something new… suddenly you understand a new perspective on what the artist wanted to capture.

• Avoiding pitfalls - Knowing the trap is there is the first step to avoid it, and investing energy in the detail work will help uncover potential problems that may have otherwise remain hidden.  While identifying and planning for these challenges adds more time to your calendar, it will pay off by avoiding the need to fix those problems later.

• Improving your skills - Getting into the details also helps you expand your skillset.  You’ll find things you didn’t know were there, or connections suddenly become obvious.  Like any skill, over time you’ll also get better at defining the detailed work, which will reduce the amount of time it takes to reap the benefits of this exercise.

On the other hand, however, I find it baffling when folks consciously avoid the details.  I’m not suggesting that everyone involved in a project needs to be at the most granular level (indeed, executives need to exist at a high level and tend not to have time for detail work), but the project as a whole needs to be aware of details.  Even something as simple and double checking settings on an email account should not be taken for granted (unless you want the whole company to see what’s in there…).  

You can always take 15 minutes to kick around your projects details with your team.  Ask them what’s missing from the plan, and then go find that devil.

You Gotta Ask

“Better to be thought a fool for a moment than to remain ignorant for your lifetime”

I’m not 100% sure where I first heard that quote, but it has helped me immensely both in my personal and professional lives.  We’ve all had those situations where we’re not 100% sure what someone said, or what they mean… or even if they’re talking to US.  We’ve all also had that lingering thought of “well, I don’t want to sound stupid….”, so instead of asking a question, we keep our mouths shut.  And we’re lesser for it.

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Our ego’s are incredibly annoying things.  While they do have some positive qualities (helping us acknowledge when we succeed, being a CLEAR signal for failures, etc), here I’m more interested in their negative qualities as it relates to the quote above.  Specifically, our fear that our ego will be hurt if we ask a “stupid” question.  There’s many thoughts on “stupid” questions (see if you can figure out which one I ascribe to based on the quotes), ranging from “there’s not stupid questions, only stupid people” to “there’s no such thing”.  Regardless of one’s philosophical approach to them, however, we still fear asking one, because it can change how others perceive us.

Speak up

This perception is heavily influenced by the culture of the group we’re with (e.g. teams with higher psychological safety will likely perceive less threat by asking questions), but that inner fear can still exist.  Knowing how to overcome that fear is an essential skill, that not only helps you get better at asking questions, but can avoid some amazingly terrible situations.  In each of these examples (and by no means is that a complete list!), taking a few moments to speak up can avoid a world of hurt.

For example:Not getting clarification on what someone needs from you… then delivering the wrong thing.

• Not asking for follow up information on a potential risk… and then having to deal with that risk.

• Not asking how to take your medication and taking the wrong dose.

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In addition to help avoid potential downsides, speaking up and asking for clarifications also helps improve how others perceive you.  Asking questions about the topic at hand tells others you’re paying attention to what’s going on.  (While I’d like to think everyone always pays attention in meetings, somehow I don’t think that’s the case).  By extension, this signals you’re interested in the topic, which is always a good thing to show.  

Asking questions also helps others understand your level of comfort and experience with the topic.  I’m not suggesting that asking questions will make others think you’re inexperienced and a fool, but rather the questions you ask will help them know where you best fit into the solution.

Personal Growth

Questions will also help you expand personally.  Not only will you learn something new (or avoid potential problems), you’ll get valuable practice asking questions.  This sounds silly, but the more you ask clarifying questions, the more comfortable you’ll get with asking questions.   This in turn, will give you more access to knowledge, and help you improve overall.  So ask away, you can never chase away too much ignorance.

Flexibility

In any given day I find myself coaching team members, managing projects, investigating bugs, being blindsided by new asks, and many many other things.  Looking back, any given day represents a crazy mix of things, and juggling them all is certainly challenging.  Despite the insanity of it all, I only really find problems when I try to control the flow things, or when I push back directly and reject doing something.  Fortunately the best approach to this isn’t to just accept ALL work that comes my way, but rather to be flexible in what (and how) I accept.

Many roles these days are anything but specific.  Job descriptions provide a rough outline of what a role is, but they can never fully capture what you’ll be doing if you get the job.  Even if they’re fairly well written, they tend to include something like “duties as assigned”, which leaves a HUGE amount of room for other responsibilities to creep in.  This craziness isn’t even touching the randomness that is smaller companies and/or startups!

Handling multiples

The wide range of randomness heading our way requires that our approach shifts from one of “I only do XYZ” to “I do a range of things”.  The trick to finding a good balance within this range isn’t to remain rigid in how we accept things, but rather to be more flexible in what we accept, and more importantly, flexible in how we reject things.  This may be further compounded by who is asking us to help out… for example if a VP is requesting help it can be a smidge harder to dodge that than someone else.

Being flexible in what work or responsibilities we accept has several benefits.  Exposure to new areas/teams/ideas helps improve our overall skill sets.  This can make our current jobs easier (by providing better context, resources, etc), and also opens doors that we may otherwise not have looked at (e.g. cultivating an interest in a new area of the company).  Flexibility also improves our relationships, either by exposing us to people we wouldn’t otherwise work with, or by giving us time to deepen existing relationships.

Being flexible in how we reject work is equally (if not more!) important.  There are times when you’ll decide you can’t/don’t want to take something on.  When asked (or “asked”), straight up saying “no”, while direct, will likely be seen negatively (e.g. “you’re not a team player”), potentially damaging your reputation but also reducing the likelihood you’ll get help in the future.  Instead you need to find a way to bend out of the way.  Suggesting alternatives (“Did you consider asking so-and-so? They’re really good at this”) and pointing out better ways to do the thing (“Instead of manually doing this, did you consider automating it?”) are great approaches that avoid the need for YOU to do the thing, while still helping ensure it can get done.

Flexibility also means being open to changing how you operate.  Especially now with many folks working from home we’ve had to change up how we work.  Resisting the need for video conferencing is basically impossible, so instead of fighting these, flex, and use them.  Sure, it requires some effort and creativity to find new ways to operate, but by making time to update team norms, meeting schedules, and other aspects of work you’ll avoid the discomfort of trying to fight the tide.

Make Time to Connect

Frequently I find myself either directly involved in, or watching, a chain of emails/texts/messages going in circles.  One person asks a question, which is misunderstood or requires followup, which leads to more questions and goes around and around and around.  It is incredibly easy to keep that chain going… after all, we know the other end is reading them, and we think we can get to agreement if we just. keep. emailing.  

Unfortunately this is rarely the case… At best, this results in wasted time as it takes several cycles to get to mutual understanding.  At worst, it results in damaged relationships.  A much quicker (and simpler) approach is to break the cycle and connect - pick the phone (or jump on zoom) and take the 5 minutes to explain things in person.

Tangled

Communications technology is a weird thing.  It allows us to instantly send messages, but weirdly this results in us being further apart instead of closer together.  This could be due to the asynchronous nature of text communication (there’s no way to tell when the receiver will read it), in the static nature of the communication medium (sarcasm, for example is REALLY hard to pickup ion text), or in the assumption that other folks will “just get it”.  Regardless, email or comment wars frequently crop up, with individuals endlessly sending messages hoping ONE of them will make sense to the other side.

We’ve all read a response from someone and wondering how the heck they didn’t understand our message.  We took so much time carefully crafting our message, only for them to somehow miss the point.  So we take more time to carefully craft a response… which is received in a similar manner on their end.  This chain eventually becomes self-sustaining and will continue indefinitely unless someone breaks the cycle (the worst I’ve seen was a ticket with 150+ comments on it running in circles).

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The problem with these cycles isn’t that the folks involved aren’t smart, or well intentioned, or anything about the person.  It’s about the medium and some assumptions we make about it.  Tools like email, slack and @ mentions are great for quickly sending a message around the world… unfortunately they also fail to capture a great deal of information.  Tone is hard to encode in text… so is sarcasm, body language, and basically all of our body language.  We tend to not see verbal communication run in as many circles because we get that additional information… we can see if someone is confused, or more easily pickup on frustration.

We also make assumptions about how we communicate and how others will interpret what we say.  On our end we assume that our message is understandable.  For ourselves this is (hopefully!) true, after all, we wrote it.  For someone else, however, this may not be as correct.  We all filter communication through our own experiences, and others rarely, if ever, have the same experiences we do.  This ties directly into how someone else would interpret our message.  Over time we get more familiar working with folks, but even WITH experience we can send a confusing message.

Finding Clarity

The trick, then, to breaking the circle of endless text communication is to step outside of it and use a different method.  Getting back to a place where non-text information is shared (phone, video chat, etc.) will reduce or eliminate many of the problems pure-text conveys.  By making communication more real-time we also provide immediate opportunities for the other parties to ask clarifying questions or point out challenges immediately.  By both reducing the feedback loop, and providing a richer communications environment, we can make our connections much more impactful.

No Extra

Extra, in some cases, is good.  Extra guac? Please.  Extra time to sleep in? Sure.  Unfortunately on a project, extra can be bad.  At best adding extra to things distorts our view of the request and makes it easy to lose sight of what is actually needed.  At worst it totally derails a project and diminishes its value to your customer.

Adding extra into our work does several things… some obvious, others much less so.  I find that instead of making things better or providing a better output, these additions detract from my deliverable.  Here’s several ways how:

Energy drain

Working on extra stuff that is “better” than our objective distracts us from what we should be doing.   We can tell ourselves we’re helping, or that we can make up the time, or that the actual request is easy to do, we’re just making it harder to complete our objective.  At best we end up putting less energy into our objective, which results in risk that we missed something important, or that the product isn’t as strong as it could be.

Diffused Focus

Working on extra necessarily pulls our focus away from what we should be doing.  Instead of critically examining our request for potential flaws, we’re day-dreaming about something unrelated.  This split focus allows us to make mistakes we otherwise would catch.  Even worse, this can result in less time to figure out the “extra” we thought was so valuable… so instead of delivering what was asked we deliver one thing that was asked that may or may not work, and another thing that wasn’t asked for of questionable use.

Missed Target

Working isn’t done in a vacuum, and we as individuals (and sometimes teams) can’t know everything.  When we make a choice to add extra to a request we’re gambling that we know what’s “best” or “right”.  While we might get lucky and deliver something that is, in fact, useful or valuable, what happens if we’re wrong?  Suddenly we have to explain why we wasted time NOT working on what someone wanted to build something that’s useless.

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I find it fascinating how hard it is to only do what is asked, and nothing more.  It should be an incredibly easy thing to do, but the allure of making it “better” is very hard to resist.  As funny as is it to say, it takes discipline to stay inside the lines.  It is true there will be times when we can push on those lines, and sometimes help redraw them, we need to be very careful not to wander outside them.  Doing so distracts us from our objective, and instead of building us up, only tears us down.

Self-Awareness

Being aware of ourselves is one of the most important skills that we can learn.  That said, from my experience it also happens to be one of the harder skills for people to learn.  Figuring out a new technology or sales technique is easy - we attend the training or we tinker with the tool.  Figuring out how YOU work, what makes you frustrated, what your habits are, however, doesn’t have a class or a seminar.  It’s not something you can REALLY tinker with or take apart.  Instead, it requires a level of critical thinking and truthfully examining yourself. This is, to say the least, a bit daunting.

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On the up-side, there are many versions of things like the Meyers-Briggs (you know, that one that tells you what color you are, and how your color interacts with other colors?) test to help teams uncover their inner operations.  (Or maybe that’s the MBTI, I always get them mixed up…).  These types of exercises are useful, however I find they usually can’t get deep enough in some areas to really dig into self-awareness.  These exercises help point out how an individual may interact in a professional setting, but it ‘s up to the individual to figure out how to apply that across the board.

This makes sense, since many of these assessments are intended to help groups of professionals work together.  They both provide a common language with which to discuss how people work (“you’re an WRST? I get it now, I’m a BEST!”) and also some general guidance for the individual on how to operate.  This works great for groups that all take it together, however, I’ve found them a lot less useful for individuals.

Choices

Work presents an interesting version of this since we can’t really choose who our co-workers are… we’re kind of stuck with whomever’s there at the time.  This differs greatly in our personal lives.  We are, to some extent, stuck with family, however, we do have a great deal more control over those relationships, and who we choose to socialize with.  This makes understanding how, and why, we will/do react in specific ways even more important… we’re consciously choosing to be with these folks instead of being ‘forced’ to.

The same techniques teams use at work to improve themselves can be tweaked to help out in our personal lives.  Some ideas include:

• Regular Retrospectives - Make time each week to reflect on the week and any areas you want to improve.  How did certain conversations go?  Do you understand why you get easily annoyed at something?

• Focus Time - Set aside specific time to take a deeper dive on one area of yourself.  I find journaling is a great approach for this; something about writing things down helps get them out.

• Active Feedback - Find someone you trust to talk over what a blindspot might be or how to improve something.  This helps break down any mental preconceptions of yourself you have, but does require a lot of emotional trust in whomever you speak with.

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This isn’t to say it’s easy… even admitting something to yourself (let alone someone else) about how you think/feel/act can be hard.  That said, it’s certainly worth it.  Getting a better handle on how you will behave in any given situation both makes you more effective and also reduces any surprises on your end.  Over time you’ll also learn more about yourself, in turn making future improvements a little bit easier.