The Leadership Coaching Exercise All Stretched-Thin Leaders Should Do

Confidence, Leadership Coaching, Mindset & Mindfulness, Overcoming Fear
10/28/22 - Nicole Wood
woman writing in a notebook

Even as the leader of a coaching company, I still need ongoing support to develop my own leadership capabilities. Even though I talk about leadership principles much of the day, I still need a third party to help me see my blindspots and overcome obstacles. 

Leading people is hard, messy and things are constantly changing. I’m so grateful to work with my incredible leadership coach, Betsy Westhoff. She helps me build a roadmap for how I personally need to evolve alongside my team and business. She listens to my monologues about what I think needs to change in my business, reminds me to take a deep breath, and then helps me channel it into something productive. In fact, this just happened about 30 minutes ago.

Why I Needed this Exercise

In the early days of Ama La Vida, my co-founder Foram and I did everything, so we had intimate knowledge of every single aspect of the business. That of course was unsustainable and undesirable, as we did things because we had to, not because we were particularly good at them or interested in them.

Over time, we hired a team to start tackling each of these fundamental business functions. We hired talented people to do marketing, HR, client success, sales and more. And still, we were small enough that we knew the vast majority of what was going on. We could probe, push and drive things forward based on what we knew to be happening and where we saw our direct reports needed support.

Now that those people have hired teams below them and the complexity of the business has continued to grow, it has become clear that it’s time for us to level up our leadership once again. Foram and I have found ourselves busier than ever because we’re still in the weeds in a lot of areas where we feel our direct reports need more support, haven’t fully stepped up yet, or where the departmental goals are not being met. And the volume is even greater now, meaning we’re stretched thinner than ever before. 

It has constantly felt like we can’t let go. People seem stumped in meetings, so we jump in to guide. Balls get dropped or things are left to the last minute if we aren’t constantly checking in on progress.

This can get chicken and egg-y. If I’m in the meeting, my team will often defer to me. If I share an opinion, it carries weight due to my title. If people know I’m involved in a project, they will rely on me to guide it. So how does one ever escape? How do you get your team to give you what you need to fully trust that they can execute without your oversight? It’s what we all want.

Recently, my coach gave me an assignment to help me elevate my leadership that I’ve found tremendously valuable and want to share with you.

Now this exercise isn’t just for entrepreneurs or those building startups. This is helpful for any leader, especially if you are new to the team, have people in new roles or have perfectionist tendencies. It helps you clearly articulate what you need from your team to free your brain and calendar for other things, more strategic things that you’d like to be doing.

How to Do the Exercise

So here’s the exercise. Go team by team and determine what you need to feel, know, and see/measure to be able to take a less active role in that team. That’s it! The beauty of it is it’s not a hack or so complex that it becomes meaningless. It’s a way to clearly articulate a need and get your team to co-build with you the most effective way to meet it.

I found success in first outlining my expectations in a Google Doc (yes, I know, not another Google Doc), but this can be done in any medium of your choice. I then highlighted each item as red, yellow or green to indicate how well I felt we were doing in each category. Once I took a first pass, I reviewed the doc with each of my direct reports in an upcoming one-on-one and tweaked it according to our discussion. We then discussed how to make the reds and yellows green.

Let’s look in more detail at each of these areas.

Feel – When observing this team and its behaviors, what do I need to feel?

This is the most nebulous of the categories, but it lays a solid foundation for the ‘why” behind each of your subsequent asks. Beyond the very tangible metrics and information you’ll of course want to know, there’s a certain sense you get from a team, how they are performing and what they are prioritizing. What do you need to feel from that team to feel that they are on the right track?

For example, as I worked through this exercise for my Marketing team, I wrote that I needed to feel we were “balancing long-term strategy with immediate needs to bring in business,” “thinking outside the box” and that “the team is in a good place.”

Know – When not with this team and its leader, what do I need to know? If I’m not in meetings, conversations, decisions, what information needs to make its way to me?

I find this category most challenging because it can easily slip into micromanager territory if you’re not careful, and also it’s the most critical for most managers to be able to let go. And of course, it tends to be the most difficult one for team members to do successfully. 

This exercise allows you to clearly spell out the:

  • Decisions that should be brought to you
  • Cadence and content of updates you need, both about the business and the team
  • Pathways to get your questions answered

To continue with the marketing example, here were some of the things I indicated that I wanted to know:

  • Key projects/priorities and progress
  • How the team members are doing
  • Any significant changes to ads strategy
  • New partnership initiatives
  • Periodic answers to strategic questions (e.g., Is Instagram driving more and more leads?)

It’s important to note that in addition to outlining these “knows,” I also worked with the team lead to determine how, when and where these knows would be communicated. Some would be delivered in reports, others would be surfaced in our one-on-ones, and others would simply be Slack pings. It’s key to match each “know” with the channel that makes the most sense.

See/Measure – What activities do I need to see are taking place? What metrics do I need readily available to tangibly track progress?

The data pieces are really fun because they are always a million times easier to dream up than to implement. We know data is limited and getting what you need can often be a heavy lift. The question here is twofold: are you measuring what actually matters to you, and do you have access to that data? 

So often you inherit an ancient dashboard or continue measuring something because it used to be important. What data points actually indicate the health of the team and correlate with your “knows?” These might be specific metrics (e.g., number of inbound calls booked per week) or insights/plans (e.g., what did we learn from our results this month and what is the plan to adjust going forward?).

To close out my example, here are a just a few of the items I need to see and measure to understand the health of the marketing department:

  • Number of leads in a rolling 7 days
  • Cost per acquisition by lead source
  • What’s performing on social and how that’s impacting our content strategy
  • What’s performing in paid media and how that’s impacting our ads strategy

Similar to with the “knows,” we outlined specifically which reports, dashboards and meetings would be the source of information for each of these “sees” and “measures.” It is likely that you may identify data points you don’t have easy or automated access to. In that case, you can determine a reasonable cadence to pull something together manually or a path to getting the data.

What Comes Next

This is not a user manual so much as a mechanism to get extremely clear regarding expectations. So much stress and frustration at work simply comes from people having different expectations and not knowing it. After this exercise, there should be very few surprises. You’re all aligned on what the team is working toward, what you as a boss are looking for and what their responsibility is to communicate to you.

The next step is to simply let go. Do you really need to be in that meeting? Do you really need to weigh in on that email thread? Is that feedback just your preference or true progress for the team?

Challenge yourself daily to step back and let your team lead. If they flounder, you can always re-engage. But you just might be surprised by how much they thrive.

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