Coaching for Sanity

When helping startups improve, especially when adjusting for new growth phases, I often find that leaders don’t really understand how to use coaching internally. When you don’t apply coaching properly, you miss out on the ability to have your people step up and increase their positive impact on the organization. For example, you might be dismissing great learning opportunities because you mistakenly assume the stakes are too high. Effective coaching is one of the three capabilities that set the best leaders apart. Let’s discuss how you can help your team grow and protect your sanity.

Coaching Hammers

Having talked to hundreds of founders worldwide, it’s clear that “coaching” means many different things to different people. We usually have a specific meaning in mind. Perhaps it’s what your first boss did. Maybe it’s based on what you read in a blog post or a book once. Even if you know it’s more complex than that, we usually view it as a binary option. Either we perform a specific intervention, or we do nothing.

Thus, I see people equipped with coaching hammers walking around looking for nails. For one, the coaching hammer might be the “set and forget” one, allowing people complete freedom to make mistakes and grow. That works in some situations but fails miserably in others.

The right path forward is understanding that your coaching toolbox needs to be versatile and adjusted to each situation. Therefore, coaching isn’t a binary option but something you choose according to what you’re facing.

Adjusting for Risk and Urgency

While they are not the only aspects relevant for tuning your coaching approach, risk and urgency are some of the most important ones. It also makes for a great example to show how widely things can change.

Low Risk/Low Urgency: These are the problems we should be leveraging most easily because they allow ample room for mistakes and iterations. If there’s a time when you should be openly welcoming people making the wrong choices, it’s here. That’s because, with the right mentoring, people can get a lot of experience working freely without too much oversight and be corrected without it being problematic. It’s also naturally an opportunity to let people do things outside their comfort zones, like expanding to new technical areas. Sadly, it’s rare. To create more of these, check out my free live session.

Low Risk/High Urgency: This quadrant is also great for accelerating growth, and even more than the previous ones when it comes to helping people realize their competency. Whereas the previous scenario allowed for a more lackadaisical rhythm, the urgency here means that with the proper delegation, people learn very quickly. These opportunities usually should revolve around execution capabilities: how to coordinate effort, communicate with peers, or keep stakeholders up to date. The low risk means however they do things, it is likely to be fine as long as they learn to execute effectively to comply with deadline needs. So, after the previous quadrant taught you the moves, now’s the time to perform them faster.

High Risk/Low Urgency: In these scenarios, we cannot tolerate many mistakes but still have the time to invest in coaching. Therefore, we can find opportunities to work with tighter feedback loops. For engineers, for example, it could mean having pair programming sessions with more senior colleagues who let them work but are there with them to ensure things are done correctly. With managers, it could mean different shadowing setups. Note that here, the shadowing side is the more senior one, observing and being ready to intervene if needed, but we default to letting people say what they’d like to do first.

That accelerates learning because they “commit” to a course of action and must acknowledge when their decision isn’t right. In regular shadowing, it’s much harder to do the same because the more senior person is calling the shots, and the mentee doesn’t have this need to choose a specific option; they are bystanders. This mode should be a bit like chick sexing—which is not as interesting as you might expect. The work of determining the sex of newly hatched chicks. This skill is essentially taught through osmosis: you pair with a senior person who shows you chick after chick and asks whether it is male or female. At first, you’re just guessing, but you learn with time.

High Risk/High Urgency: This is the Asterisk quadrant. Yes, if you’re dealing with someone that has to be done right and now, you’re not likely to have a lot of simple coaching injected into the process. But there are two things to keep in mind. First, as you’re dealing with such a case, you should at least be operating in the regular shadowing mode, where people observe very closely to see how things are done in real-time. Try and communicate as much as possible your thinking process. If possible, ask them what they think in between, like in the previous section.

The second aspect is where the asterisk comes in: You might be getting into too many of these situations precisely because you lack all the other coaching opportunities. That means things are more likely to escalate to the point where you no longer have other options. So, if this happens regularly, consider your day-to-day operations. Further, extract any learning possible from these. For example, after these occur, try to distill from them the decisions that were made and compile guidelines or training materials so that people can do it themselves the next time.

That’s all part of creating an organization that delivers with a sense of urgency without an emergency. For more about that, join my free session, Sparing the Midnight Oil.