The Leadership Exit

Making the decision to leave is never easy.

It’s easily doubled when you’re the Leader of a team because not only are you now leaving an organization, you’re now leaving a group of people that you have invested an incredible amount of energy into their own personal and team growth and development that to leave feels like betrayal.

They bought into the story.

They listened to everything you had to say.

They jumped higher than you asked.

They believed.

And now you are leaving them. Or rather that’s what you’re made to feel like when you make this hard decision to do so.

“You’re abandoning us”

“You’re leaving us behind”

“Why aren’t you taking us with you”

“How could you?”

There are many emotions at play here when you decide to leave and most are coming at you.

Let’s dissect a few of the most prominent ones here.

You’re Not Leaving Your Team

It’s time for you to move on to new challenges and opportunities. Leading a team is like being a parent, there is a moment when you know it’s time to let your kids go, spread their wings and start leading themselves.

Every Leader knows when they’ve hit this point with a team – “I’ve done enough here and what comes next will only be incremental. You need more, you need a different approach, you need someone else.”. This isn’t an easy realization for a leader to come to, but it’s one that is realized from the view that they want their team to continue to grow, become stronger, better and share that wisdom with others.

When the Leader’s involvement is only going to result in incremental returns, it’s time for them to make the exit.

It’s Not a Betrayal

And if your team thinks it is, then you should have left much sooner. Your team is now dependent on you for more than you had originally hoped and they are fearful that without you, they will fall apart.

Fear is a powerful emotion and a Leader should never stay if the team is fearful they cannot survive without them (the Leader). If this is the case, then you haven’t done the proper work in preparing your exit strategy and ensuring they are setup for success for when you leave. A well organized team should be able to survive in the short-term without their Leader and keep things going through what has been taught to them.

Don’t fall into the trap of being made to feel you are disloyal or have betrayed your team, you are giving them the opportunity to grow and develop.

The Bought Into You



Your team bought into your plan, they executed and delivered on what you asked them to do, what you inspired and motivated them to do, what they raised up their own games to do.

This isn’t a bait and switch or a pulling of the rug from underneath their feet, this is your team trusting you to lead them, you leading them and no matter where you are in the delivery of your plan, they are being successful and continue and will continue to be successful.

What everyone tends to forget when you are leading a team or a project is that this IS THE ONLY  team and/or project that you will EVER lead.

But it isn’t and will never be and for you to continue growing, you will need to work with different people, validate different approaches with a new group of people.

In the end, you might end up working with some or all of these people and that is the best experience because not only did they buy into you at this moment, but they are ready to do it again, this time without having to go through all the Interviewing and Identifying and get right to Delivering.

Don’t fall into the trap of changing your mind about leaving because your team doesn’t want you to leave.

Focus your energies on setting them up to take over from you with the remaining time that you are working them. Over that period of time, their emotions will subside and will turn to being happy, excited and proud of the tough decision you’ve made. You’ll inevitably have many one-on-one conversations that will turn out to be some of the most encouraging conversations you or they have had during your tenure, enjoy them and know that you’re making the right decision.

But don’t change your mind, over time you will resent the decision you made and depending on your team, their attitudes might change or shift as they realize you will always be there to catch them if anything goes wrong and they’ll slowly start to question what your level of commitment truly is when faced with tough decisions.


Collaboration’s Biggest Challenge

A few years ago, SLACK was the messaging darling, enabling quick, simplified messaging with minimal setup and management for administrators.  In addition, it boasted a robust API/Integration framework which let it do what so many collaboration applications to date had struggled with – get inside everything you work with.

Or rather, you get inside SLACK with everything you work with.

Fast forward to today and there are not only a number of challengers to SLACK but also SLACK has been hit by a few complaints about being “too much”, “always on”, “never able to get away”, etc, etc, the list goes on.

This isn’t a SLACK problem though, this problem has been in existence since the first iteration of that green jellybean icon came to represent your availability – you are here, you are available, let’s get to work.  That little icon came to represent not only your availability to get work done but also an indicator of when you are available to get work done (read: how much work are you putting in, how later are you up).

Collaboration’s biggest challenge to autonomy and not micromanaging your team has always been that little green icon.

How do I know where they are if it’s not green?

They’ve been away for so long, they must be doing something else?

Why aren’t they answering when they are green?

It’s the perceived notification that someone is available and ready to do work for you – that’s how it is interpreted but what it was never meant to show.

Want to know how pervasive the colour schemes are in messaging tools?  Look no further than them all using similar schemes – green – available, yellow – maybe, red – busy – they flow between different systems so we don’t need to relearn anything.  And just like a traffic light, they mean exactly the same things to a user.

But the question for the traffic light – Would you leave it on green all day long? – probably not, because eventually, it’d burn out.

When email took on the collaboration challenge it did so without presence, asynchronous communication – “I’ll get back to you when I can because I could get busy” – which unfortunately turned into the simplest of messaging protocols that allowed and enabled people to SPAM us with updates on everything and anything.

As much as we want to make it, Collaboration’s biggest challenge will never be the technology, the protocols, the AI to reduce message flow, where it’s hosted, whose hosting it, etc, etc, etc.  It will be the trust we put in each other around presence and messaging to ensure that those boundaries are preserved and supported.

Think that’s an easy way out?  Then here’s a question for you – What is your company’s collaboration policy and does everyone know what it is and how it works?

Doubtful, if you do fantastic and if you do, that means this post wasn’t meant for you, it’s for the rest of us that are working against that little green jellybean trying to find the right way out.


Lead them in the Middle

Your First Team Meeting is critical to getting things underway with either a new team or project.

How you start will set the tone for how the project will kick-off and where your team will look to focus their energies.

In the beginning, like the song, “Everything Is Awesome” in the beginning, simple because it’s all new, emotions are at a newfound level of excitement, goals have been set.

You’ve set the groundwork, the plan, the direction, the path to go down, but apart from that – but you haven’t started yet.

Nothing has been done, so everyone is happy with the dream.

Fast Forward to the end of the project, the team has come together, they’ve gone through the final pushes of people coming in early, working late, sweating more then they usually do, doing whatever they can to get this project/product out the door and make it a success.

The team has done in so again, emotions are all happy because the release has gone out the door.

If you haven’t realized it – this is where you many of the great team quotes originate from – how the team came together to become a success, how they fought through adversity and change to deliver, how they never gave up.

There is enough literature on how to start and finish any project to keep you reading well into the afterlife.

But what about the middle?

What’s happening in the middle?

What’s going on when all that code churn is happening?

When the team is having to up their growth quotient by learning on the fly and still delivering?

When frustrations over not hitting performance targets are starting to set in?

When the team is feeling worn out and knowing that they have much more work to put in?

This is where Leadership matters, this is where Good Leadership matters – Leading in the Middle.

  • Leading when things aren’t perfect.
  • Leading when everyone is complaining.
  • Motivating those around you to keep going.
  • Keeping your head when things don’t go right.
  • Knowing when your team needs a break or they will be broken.
  • Understanding what minor things manner in the grand scheme of the whole project.
  • Giving your team leeway to try new ideas and let them fail.
  • Insulate that failure and not blaming it on them.

If you can do all those things, then you are already on the right path to Leading your Team in the Middle.

The most successful teams are those that were able lead well in the middle when things became murky or the team started to struggle because that’s what every team goes through.

The middle is never perfect, it’s never clear, it’s never straight forward, how you lead in the middle does not define how you will finish, but rather who wants to start with you again on the next project.

Will they come back for more?

In the calm moment of reflection that happens after the delivery of any project, will they go back there with you?

When lead correctly, in the middle, the team is ready to jump onto the next challenge, they are sold before the project is even announced, it’s not a question of If the project will start but When.

If you start off with the right objectives, lead well in the middle, the end will take care of itself.  If you start off strong, mess up in the middle, the end will eventually take care of itself, but not as well as it could have and you probably won’t get another opportunity to start again.



The Leadership Change Goal

If you think you can change your team’s behavior, direction, and course in thirty days and have them executing on that change – you need to reset your goals.

Leadership is a long game, the more members on your team, the harder it becomes to implement the change you know that the team needs but that the team cannot reliably implement because there are more variables in the mix.

Coming in with a list of demands for behavior and direction change will only serve to confuse your team.

You need to start small and focus on incremental growth and adjustment.  If the team is not delivering, your efforts should be focused on the behaviors and attitudes that shape that delivery.

Are there internal or external threats that are preventing them from being successful?

If so, what small investments can you make that can yield larger gains in the next thirty days to precipitate those bigger changes?

If your Goal is for the Team to “Deliver Better” the first step is to work with the team to identify what delivering betters means to them and everyone on the team.

At that initial discussion, there should be zero discussion on the solution to that goal.


Because this is the first time you are discussing it with your team.  The first opportunity they have to respond, to come up with a suggestion or ideas on how that problem can be solved.

You need to hear what they have to say because this will affect the solution that together you will implement.

In holding that first meeting, you will have accomplished the goal towards getting your team to understand the problem and begin the task of owning it.

If done right, over the coming week while you are working with your team on potential solutions, team members should be coming to you with additional questions on the final goal – i.e., can we do this as well?

You want this, you want their involvement, you want their ownership.

While fielding these questions, this is an excellent opportunity to bounce ideas off of your team members on how to solve your team’s problem and what steps you can take to get there.

When you circle back with your team the goal of that second session should not be about timelines it should be about the steps needed to be taken to achieve the goal.  This is key to the success of your plan as not everyone will understand the steps that go into achieving a goal and the timelines will be dictated by that understanding.

Once enunciated to your team, the path that you and your team are going to take will then be clear, who will be responsible for what and how the final goal will be achieved – the conversation can now switch to how you and your team will achieve this goal and on a what schedule.

We are constantly bombarded with news and information that teams need to keep changing now and to meet that demand as quickly as possible.

Even during the development of a short-term project, say four to seven months, the pressure is just as great to “produce results” and “show change”.

History has always proven that the team that manages by Ownership and Adoption and treat Change as a marathon are more likely to succeed in that endeavour.

Don’t be the Leader that “hopes” the change gets implemented, be the Leader that knows when it will be implemented.

Hiring the Right Person for the Wrong Job

Hiring people is the hardest part of any organization’s growth. You have this perfect symbiosis of people working together in your environment, your customers and market share are growing and now you need to add to it.

You need to add to it for all the right reasons – they are overworked, you need more specialized skills and you’re starting to think about what happens if someone gets hit by a bus on the way to work.

You needed to grow the team and you needed to do it yesterday.

But you can’t because you’re worried you might hire the wrong person that doesn’t fit into your culture, that doesn’t jive with everyone else, that breaks the symbiosis that you have going on now.

That culture that you are so fond of, is going to change no matter who you hire, that culture you have is what got you to where you are but now, just like your team and your organization, it needs to evolve, it will evolve, it will grow.

Fixing a bad culture fit is an easy fix – let them go, fire them, drop them. You can feel out a bad fit after a few months, take correction action and move on and if anything this will strengthen the culuture you have in place.

The harder problem to solve is when you’ve hired someone that fits in great with the team, has great skills where they contributiong but when you take a step back to look at what your organization needs to level up, it’s not them.

Maybe you didn’t realize it until they started (and the real issue was exposed)?

Maybe you had an inkling of what you needed but wanted to hire with what you knew and that was easier.

Maybe you hoped this hire would be a Jack of All Trades and lessen some of the impact on the team in that area.

Whatever the reason – you have a great new resources not doing the job you need to have done to ensure your organization’s future growth.

You hired a Developer, you really need a Product Manager.

You hired a QA Lead, you really needed someone someone onsite with customer running through Beta trials.

What do you do?

Do you shoehorn them into something they don’t want to do and see where it goes?

Are you upfront with them about the mistake that was made and see if they want to make a career switch of move on?

Do nothing and hope it all works out and that piece that you really need gets done at some point in time?

I’m sure there are other solutions that you can think of but all these solutions revolve around that new team member when you need to be thinking about your organization and the current team you have in place. Your current team is looking to you to make the tough calls on how to direct the company and keep people from burning out, your team is looking for you to be focused on where they should be in the next six to twelve months and line them up for success and your team needs you to know when to change course with what’s best for them.

When you’ve hired the wrong person for the job, the problem will not fix itself unless that new team member is looking for a complete 180 career switch but even then they’ll be starting at ground zero with none of the experience and knowledge that goes along with it – translation – you still lose.

Hiring the right person for the wrong job is only acceptable when you’ve got the funds for it, when you’re cycling towards mass growth, you don’t have the time or the funds for it so make sure you know what you need before you bring them on.

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