6 Steps to Make Yourself Obsolete as a Leader: Part 1 - The Art of Delegation

In my previous post Your Job Is To Make Yourself Obsolete, I talked about how our job as good software engineers is to make ourselves un-needed, and how this rarely translates well for us when we go into leadership or management positions, even though it should.

I highly recommend that you read that post first, which talks about the importance of making yourself obsolete as a leader. Because in this and the following blog post, I’ll share my highly opinionated - 6 (not so) simple steps program for making yourself redundant as a leader or a manager.

Ready? Hope you got some comfortable shoes, this is going to be a long climb…

It’s a Long Way Up There - Photo by athree23 on Pixabay

Step 1: Put Your Ego Aside

The fear of making oneself obsolete is an existential one.
If you are not going to do all those specific things you were so good at doing, who else will?
Well the answer is literally anyone, and no, that doesn’t make you worthless.

The first step is understanding that your value does not come anymore only from doing the things you are good at, but from providing the high level vision for others and enabling them to do the things themselves. And even if you might be the best, most talented and responsible person out there, it doesn’t mean others can’t be as well.
They just need that direction as well as time and help to get there, your help.

You need to understand that your top priority right now is making sure others are equally as good as you are at getting things done if not better, and that they all share the same vision as you.
This can only happen by you consistently mentoring and coaching them, with the sole purpose of eclipsing you in the near future.

Step 2: Hire Competent People that You Trust

This one is slightly controversial, and I had back and forth thoughts if to include it or not.
The reality is that you will never have the perfect team, there are always going to be skill gaps, be them technical or of the soft kind. You will never have enough people, they will never be senior enough or have enough veterancy in your company.
This is something you need to accept and embrace, and work on actively bridging people’s gaps in skills and seniority.

However in some cases you might find that the only way to move forward goes through reconsidering the composition of your current team.
This happens when the gaps in skill or engineering maturity are just too large to bridge within a reasonable time, and when you believe that the potential and growth momentum for some people are simply not there.
It is rarely the case and rarely is this true for the entire team, but in cases like these, you have no choice but recruiting one or two key people that can act as fertilizers for the rest, even if it means letting go of some team members to make room for new ones.

If you go down this path, you need to remember that your goal is not necessarily hiring people that are identical to you or are even like-minded, you should very much seek diversity.
Many of us mistake conformity to our personal cultural values as a signal for success in other people, which is incredibly biased, but simply how our brain works. So you always need to double check if you are looking for new people because of objective reasons like skills or subjective reasons like how much they agree with you.
At the end of the day, your goal is to find people in which you see the potential for growth you can’t find in your current roster, the people that with some help will be able to take gradual ownership of the type of responsibilities you can’t let go of today.

What does this mean in practice?
If you are the key technical brain of your team, you need to look for someone that can grow to be a technical lead. If you are the only “people person” in your team, you look for someone with soft skills that can grow to lead communication and teamsmanship. If you are the only one with the capacity for good project management, you need someone that is highly responsible and detail-oriented that can grow to lead the execution of complex projects.

Ideally you should always be looking for these qualities and growth potential within the people that are already there, hiring should definitely be your last resort.
You must always remember that the perfect person does not exist, so you might end up looking forever. Check yourself whether you are actually trying to find the right person or maybe you are chasing a unicorn as an excuse not to push your team forward.

Step by Step by geralt on Pixabay

Step 3: Delegate Everything and Overshare Context

Now we are getting to the real meat and potatoes - Delegating.
No one is good at delegating at first, and it usually splits into one of two reasons: Either you don’t feel like your team-members are capable enough do the type of things that are within your responsibility, or you are trying to “protect them” by not giving them more work. Both might sounds like legitimate reasons, but they are hiding some major blindspots.

If you don’t feel like your team members are capable enough to take on additional responsibilities and do things as well as you do it’s a shame.
But guess who’s job it is to train them to be able to… That’s right, it’s yours!

No, things will never be done exactly how you would have done them yourself, not unless you micromanage people to death, and that’s not a valid option either.
You need to come to the realization that things might happen differently than the way you would expect them to happen, and thats fine. Things might fail at times or not be done in the same quality as you would have done them, and that’s also fine. You didn’t do everything well the first time either and it took you a while to learn, so why shouldn’t people in your team get the same opportunity?

On the flip side of things, some think that by masking away the complexities of leadership, or even just by taking on to themselves the small annoying tasks and meetings no one likes, they are doing a service to their team. They are “protecting them”.
This truly might originate from an act of altruism, but it can also originate from the fear of overwhelming people or just pissing them off, which is something no one wants to deal with. That of course is also a fallacy.

Growth doesn’t happen in your comfort zone, growth happens when you are pushed into things you feel uncomfortable doing. New skills are not developed doing the same things you are used to do, but by being introduced to new situations and paradigms. Lastly, what we might perceive through our very subjective lens as annoying, if framed correctly, others might see as an opportunity.
Think about how you’ve accumulated some of your skills and you too will realize it didn’t happen just by sitting quietly working on you tasks. A lot of those skills got built doing things outside of your strict work definition, outside of your comfort zone. So why not give your team the chance to do that as well?

So what should you delegate? Ultimately, almost everything.

Here’s an exercise for you, think about all the things that you do during your work week, every single thing, and put them in mental buckets by the type of skill or expertise those require from you.
Now for each bucket ask yourself “Am I the best person to do this job?”, if you said “yes” ask yourself once more “Am I the only person that can do this job?”. Lastly, ask yourself “Is it impossible to train someone to do this job within 6 months?”.
Are you with me so far? Good.

Now re-bucket all these items based on your answers.
The first bucket is for things that didn’t even make it in the “I’m the best doing it” category, let’s call this one the “I’m not the best” bucket. The second bucket is for things where “I’m the best”, the third bucket for things where “I’m the only, but I can train”, and lastly the forth bucket for things “Impossible” for others to be trained to do within 6 months.

The 4 buckets of responsibilities

Everything in the first two buckets you can delegate tomorrow morning, yes even the things in the bucket that says you are the best at them… Remember Step #1? Put your ego aside.
Obviously don’t do it all at once, it should be a gradual thing, but you need to start doing that.

Now the third “I’m the only one that can do it, but I can train someone in 6 months” bucket. Call this one your “training backlog”.
At any given point in time, every single member of your team should be training on doing at least one of the items from this bucket.
You need to plan this training well and allocate time for it, which should now be possible for you after delegating everything in the two other buckets!

Lastly, the forth “impossible” bucket.
This one should be a very small bucket and if it is not, you should probably redo this exercise and rethink things.
This bucket will usually hold the HR aspects of your role if you are a people manager, things like compensation, personal one-on-ones, performance reviews. It will hold strategic responsibilities like defining and communicating the high level long term vision and goals for the team, as well as planning and pushing cultural changes.
Lastly it will also hold all kinds of “management only” type of meetings, you know, the ones where we all wear funny hats and sing hymns to the gods of software engineering. But that should be about it.

If there’s a lot more than that, it might mean you don’t have people that you believe can learn to do the things you do within 6 months. Which either means you judge them too harshly or you need new people, in which case go back to Step #2 again.

When delegating you need to frame every task and opportunity given as a growth opportunity, and you need to be transparent that as with any type of growth there’s going to be hardship and risks.
Your goal as a leader is to proactively build this growth plan through delegation. Your goal is to endure these risks and be accountable for possible failures, but also to leverage those failures to mentor those you delegate to on how to do things better next time.

Vision, Context and Framing are the Roots of Inspiring Others - by geralt on Pixabay

As you delegate more and more of the things that are within your zone of responsibility, it’s important that you not only give things away, but you also share the full context for them that usually resides only in your head.
There is no such thing as over-communication, and only by explaining things at length, even those that seem trivial to you, you can ensure that you don’t only pass over the responsibility and ownership for things, but also the history, the mindset and the reasoning behind it.

You might be tempted to “teach people to swim by throwing them into the water”, which means saving time by not over contextualizing and letting people figure things out on their own. This can be an affective approach and I have seen great managers use it with success, though it has caveats.
If you choose this path you need to be transparent that you are purposefully doing it, ensure it is framed as empowerment and not neglect.
You should also think wisely who you choose to take that approach with as it doesn’t fit everyone, and be available to fill in the missing pieces along the way when needed.

Regardless of how you approach it, you should make sure that the person you delegate to understands why you are asking him or her to do a specific thing. What is the importance of it, who it affects, and how it fits in the bigger picture. You can never over-share but you can always under contextualize, so it’s always best to err on the side of caution and be overabundant with communication.

Step 4: Train Your Successor

The last step for this post, and here’s another doozy for you.
If you are working in a high growth environment and within the first year of your leadership position you haven’t already identified or hired the person that is going to replace you, and if you haven’t started actively training him or her to do so, you are failing at your job.
Yes, that’s what I wrote, if you are not training the person that is going to take you out of your current position, you are not doing your job well.

While deep inside you might know this is true, it just feels so scary.
If you end up training the person that is going to be your replacement, you will end up being… well, replaced.
Does that mean you are setting the scene and laying down the red carpet for your own unemployment? How can you afford doing that?
Well think about it this way: How can you afford not to?

If you don’t train your successor, your chances of moving up successfully in your organization are so much smaller. How could anyone afford to promote you if there’s no one else that can take your place?
Even when the opportunities do arise, and they do very quickly in fast growing companies, your company would much rather choose someone that have already trained his successor and will make the transition so much easier.

Even if you don’t have such aspirations to move up or horizontally in the organizational tree, it’s still in your good interest. Because as I’ve written on the previous post, like most human beings, you probably like to take a vacation now and then, and it’s so much easier to go on one with a clear mind knowing that there’s someone that can maintain continuity even when you are gone.

This doesn’t mean that there needs to be a set date and time for when you plan to have this person replace you, or even have this openly on the table as an option. You shouldn’t be promising anything you don’t have any control over. However you should be very transparent about how you are going to invest in this individual by mentoring and delegating those specific responsibilities you hold the closest.

Remember that the success of your successor eventually translates on to you just as much as it does on to them, if not more so, and you should actively pursue on helping them achieve it.
The skills you will learn while doing so will be the ones that end up making you a better leader or manager either in this position or the next one you will grow into.

The next step is always the hardest - by geralt on Pixabay

The pursue of continuous delegation is really a never ending journey. New responsibilities keep popping up or changing, and managing it in-and-of-itself is a complicated matter.
You need to be a force multiplier for others, you need to continuously manage the team knowledge map and mentorship plan. You need to communicate context and lastly you need to give lots of constructive feedback.

You also however can not neglect your personal technical skills and deep understanding of what your team is doing, because those are foundational. Delegating does not mean losing touch with what is actually happening in practice, it’s just a layer of “automation” and “abstraction” putting you at a higher level of leadership. You need to stay in touch and you need to stay technical, or to quote Camille Fournier:

“The pyramid of success looks like a foundation of strong technical skills, add in some other stuff and top it off with “don’t be a jerk”.

But taking this back to where we started, making oneself obsolete as a leader doesn’t end with building the team and delegating them responsibilities.
On the next post we will discuss the last two steps which are much broader and more complex and have to do with your role in orchestrating the team as well as leading strategy and decision making. Both of which are key things to focus on when making yourself obsolete.