Coaching Inception

Especially if you’re a first-time leader, you “know” that coaching is the “right thing” to do in your organization, yet have issues with actually kicking it off. Perhaps you’ve never seen how proper coaching should look like, or you’re worried about your ability to even help your team. Here are the five most common worries I’ve heard leaders mention—often only in private because they felt bad admitting them—along with what you can do about them. Can you make coaching your new habit in the new year?

“I’ve never even experienced coaching”

How can you do something if you don’t know what it should look like, right? I admit, chances are you’d be a better coach, having experienced it yourself in the past. That doesn’t mean that everyone you lead from here to eternity must suffer the same lack of growth. Just like so many leaders and managers in tech got thrust into those positions without any real training, sometimes you have to do these things without a great role model.

Start simple, like reading a good book on the subject, and start experimenting. You can be honest with your team and admit that you’re just starting as well, so they can feel free to provide you with feedback about this. Use these regular meetings to ask some questions, provide some feedback, and make room for those on your team to consider what they need. Oh, and you just might want to get some coaching yourself.

“I’m not the best engineer”

Frankly, I never really understood this. Team leads, and sometimes even directors, told me of issues coaching their ICs because they knew they weren’t as good as their ICs. Perhaps I don’t relate because I’ve never had a manager who was better technically than me (I kid! Partly). Yes, if you know the technical parts better than them, it would make it easier to mentor them along with the work. You’d be able to suggest alternatives and spot issues.

Nevertheless, you don’t have to always know everything better. What’s more, that’s literally impossible in any project that’s not trivial. First, you’re not even an engineer anymore, why would you be expected to be the best? Second, are you supposed to be better at any topic than everyone on your team combined? I doubt it. Coaching here should be about helping them do the work better, giving feedback so they learn, and, if needed, ensuring that they get the proper mentoring and training to grow some more. That mentor could be you, but it could also be someone else on the team. Yes, mentoring and coaching are not the same.

“I’m an inexperienced manager”

Kind of similar, I’ve seen cases where first-time leaders found it problematic to lead the managers under them. This is especially common for CTO co-founders who never had senior leadership roles and now have to work with their growing organization. The issue here is subtly different because you are a manager like those reporting to you, and you might feel like they know some things better than you. So?

Does every Olympic champion have solely previous world champions as coaches? Does being a coach mean you always have to have all the answers and have gone through every single similar scenario in the past? No. You should be methodical and add more tools to your arsenal as you mature as a coach, but you can provide value immediately. Sometimes, all we need in order to grow is some honest feedback and someone asking us the right questions. And if you don’t start now, you’ll never become a better coach.

“People might get worried”

In companies where the culture didn’t naturally include regular feedback, one-on-one meetings, and similar aspects of coaching, the sudden introduction of coaching could be jarring. I’ve seen cases where someone interpreted this as being in trouble or almost as if they were on a PIP, regardless of their actual performance. Yes, this might happen if you start changing your behavior out of the blue and without communicating it properly.

So, communicate properly. Explain to your team that you’re starting an experiment of coaching. Tell them what you hope to achieve, how it will work, and what to expect. Make this public and not something that they learn about from receiving an unexpected one-on-one invite with the boss (no one likes those).

“I don’t want to open up a Pandora’s box”

Lastly, you might have concerns that by creating these one-on-ones, giving and asking people for feedback, and actively trying to help them grow, you’ll be inviting them to start asking for things. Many times, managers told me they feared having everyone on their team ask to get a managerial role next (and, for a couple during the highs of the post-Covid market, it was actually like that).

Like in the previous section, this all boils down to your expectation setting and how you communicate things. Coaching and asking someone about their long-term goals doesn’t mean that you can promise them they’ll get it. It does mean that you’re putting things on the table and will start discussing them. Would you rather have people tell you months or years in advance that they’re thinking about such moves or only find out once it’s too late and they’re giving you their notice?

If you’d like to grab my free coaching framework short ebook, it will be going out to my newsletter in the next couple of weeks. Sign up below so you’ll get it. Go forth and coach. You’ve got my permission.