Ensuring that coaching happens regularly in your organization and that each person grows is a basic tenet of any healthy tech organization, as described in The Tech Executive Operating System. Nevertheless, as I help companies implement a coaching framework, there are “exceptions” that regularly creep up. How should you handle those whose coaching isn’t “easy”? Let’s go over some of those archetypes with specific steps. That will make handling them easier and help you handle similar yet not identical cases with more context.
No Single Fault
First, let’s address our mindset. Even though these people might be less “easy” or “ideal” as employees being coached, that doesn’t mean that they’re necessarily in the wrong. There are three factors in any such situation. One, of course, is the employee. However, there are also two other factors: who’s coaching them and the environment—the company.
Some of the exceptions we will cover below would be problematic in a certain context but not in others. Those depend on how the managers view these and the company’s situation. For example, sometimes coaching someone who’s aspiring for promotions is problematic if the manager has a “gatekeeping” belief (even unconsciously) that each should take X years to make such a transition, just as they have had to go through. Others might present an issue solely because the company is not likely to grow in the near future. All this is to say that you should assess all your coaching issues with these other factors in mind. Is it objectively a problem, or is our context making it problematic? That won’t solve things, but it can help you view it differently and better help the employees and the company.
Status Quo-ers
You might know them. These are usually engineers who are quite good in a specific skill set and are content. What’s a manager to do? Let’s start by agreeing that not all growth is purely technical. So, someone who only wants to work on the backend code and is productive doing it could be fine technically (unless the company doesn’t need someone to only do backend). However, I’ve yet to come across someone who is perfect and couldn’t improve at anything.
Think about soft skills that could be improved and even simple technical-adjacent skills like mentoring others. They cannot just keep going on autopilot and expect to remain “sharp.” I strongly believe that those who stop learning and challenging themselves deteriorate.
Lifers
An asterisk for this group is a subgroup that’s not interested in improvement because they’re already busy with something else. Perhaps life’s too much as it is. It could be someone who’s working on a side hustle, taking care of children, helping parents, etc. When that’s the case, and the employee is performing well, I think it’s ok to come up with simpler coaching goals that are less of a “stretch.”
Lack Ideas
Similar to the previous case, yet different, this is about an employee who’s willing to set some personal growth goals and work on something but is just coming up short with any ideas. As managers, when you have someone who’s “easy,” performing well, and not demanding, it’s easy to ignore them. After all, the squeaky wheel gets the grease, and these people aren’t as clamorous.
However, that’s doing them a great disservice. Think about soft skills. Give them feedback about their performance. Perhaps hold a small 360 review to collect feedback from their peers and colleagues to find possible areas of improvement. You don’t have to come up with all of the ideas by yourself and stop thinking that each coaching goal should be world-changing. Sometimes, people do well enough, focusing on how they communicate their thinking or manage their time.
The Oblivious
You’re talking to someone who has trouble even speaking up about what you should have for lunch but who suddenly asks about a managerial role as part of their coaching and desires. You know that they, as things are, this person would never get such an opportunity. What do you do? Many leaders shy away from really handling this and instead bluff.
They give these oblivious employees no real feedback—fearing “hurting their feelings”—and instead let them continue their fantasies. Stop it! Your role in coaching these people is to help them realize where they really are. What are the gaps you see? Which skills should they make a noticeable improvement at even to be considered? Work on that (or tell them honestly to consider something else).
Unrelated Wishes
An engineer asks to get time to learn a new framework that’s unrelated to what the team is doing. Even worse, there are other more pressing areas you’d like to see them improve at. This is an easy one: if someone’s performing well, it could be ok to indulge them from time to time (e.g., one quarter of the year, as long as it doesn’t harm their work). However, otherwise, this is just creating a kindergarten mentality where people can work on things that make no sense.
Better Than You
I’ve seen this happen with very senior engineers, and their managers felt they had nothing to teach them. It’s also the case sometimes when you’re managing managers, and some people might already “know everything you’ve got to teach.” If you decide to do nothing in this scenario, you’re increasing the odds that they’ll get the same impression and decide to leave.
Instead, work with them to find out what they’d value and could improve at. I’ll let you in on a secret: you don’t have to know it better than them to help them. Perhaps you can find someone else in the company to mentor them around a specific issue. Maybe you could decide to create a book club to discuss leadership issues together, get conference budgets, or even hire a coach. The worst thing is assuming someone will make do by themselves in these scenarios. They might be fine but won’t respect you as a leader.
Wants Your Job
Literally or figuratively. For example, you might be a cofounder and have some early employees say that they want to learn from you in order to eventually start their own company. Or it’s someone who openly says they’d be interested in having a VP role down the line. Perhaps I’m naive, but my default assumption is that as long as there isn’t any evidence that this person will play nasty politics and try to oust you, there’s nothing to worry about. Stop being so worried, and help them.
Will you be investing in them only to have them leave when they are finally ready to take on more responsibility internally? That’s always a risk that you have to live with. What other option have you got? Neglecting them and having them stay?