How does a manager teach their team to do what they can do?

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A common theme I hear from managers is that they struggle to teach people on their team how to operate in the way that they do. Especially if it’s a soft skill or a judgment call.

Some of our soft skills and instincts come naturally to us. Some are honed from years of experience. But rarely do we think about exactly which skills and experiences got us to where we are.

And it’s really difficult to think about how to teach it to someone else! How is a manager supposed to teach someone a skill that they were never taught? Shouldn’t it just come naturally to everyone?

I definitely thought this way. At least, I used to think this way until I had the following conversation with my manager:

My manager: Your team seems to be performing really well. Which of them do you think are ready to perform at your level?

Me: Hmm. Yes, my team is fantastic, but they have less experience than me, so I wouldn’t expect them to be able to do all the things that I do at this stage.

My manager: That’s fair. What are you doing to close that gap? How are you helping them to build the skills that you have that they’re missing?

My manager helped me realize I wasn’t helping anyone. Not my team, who needed those skills to grow. Not my manager, who wanted to have more coverage and an evolving team. And I certainly wasn’t helping myself, since I would need a succession plan if I ever wanted to get promoted into a bigger role.

As I embarked on the process of upleveling my team, I discovered there were four key steps:

• Understand the gaps
• Deconstruct how you do what you do
• Teach the skills
• Provide the opportunity

Understand the gaps

I’m a huge proponent of clearly documenting and providing feedback on detailed performance expectations. However, I’d always focused on using those expectations to evaluate my team members in their role. I hadn’t thought much of how they would do in my role.

An assessment of my team members against my skillset is more comprehensive. It would include things like:

• How would they handle difficult stakeholder issues that they currently escalate to me?
• Are they able to provide coaching/mentoring to more junior team members?
• Are they able to plan and scope initiatives for themselves and others?

Great managers cover a lot of critical tasks. If your team members are individual contributors, they might never have had the opportunity to get experience in those areas.

One useful guiding principle: If you were out of the office for a few weeks, could your team members step up and cover for you? If not, which areas would have the biggest gaps?

Develop a short list of areas where you have strong experience, but your team doesn’t yet. Focus on those that are most relevant for them in the near-term.

Deconstruct how you do what you do

This is the hardest step. It’s challenging for two reasons:

• Many of your skills come from years of practical experience that you can’t easily translate into a quick crash-course training.
• Some of your skills may come from your own natural abilities, and you were never trained yourself. How can you train someone else in what came naturally to you?

I sometimes liken it to looking at a magic-eye picture. Some people can look at it and immediately see the 3D optical illusion. Other people can stare at the picture for hours and they just don’t see it. But you can’t just tell those people who aren’t seeing it, “It’s right there! Why don’t you see it? It’s so easy to see it!”

Magic Eye

So how do you help people see it? You learn how to deconstruct the process that is happening automatically in your brain. Slow your thinking down so that you can capture the steps that your brain is churning through in seconds.

Think about:

• What skills are you tapping into?
• Are you drawing from prior experience in similar situations?
• Are there any frameworks or best practices you learned that guide your thinking?

Let me walk through an example from my own management experience.

Dealing with challenging stakeholders was a common hot topic in my team. Often team members were working with leaders who were senior to them, and would sometimes put them in difficult situations. This could include things like asking for more support than we’d agreed to, not showing up to meetings, or being disagreeable with other stakeholders.

Frequently in 1:1s, my team members would ask, “How do I deal with this person? It’s disrupting the project. I don’t know what to do!”

Fortunately, I did know what to do. I’ve dealt with more challenging stakeholders than I can remember. But I didn’t want to just tell them what to do — I wanted them to be able to solve it themselves.

So what went through my head when I was asked about how to handle a difficult stakeholder? (Aside from, “Oh no, not this again!”)

Here’s a sampling of questions that run through my head when I am personally dealing with a challenging stakeholder:

• What do I know about this leader? Has a similar situation occurred with them in the past?
• If I haven’t worked with this leader, do I know anyone who might have insights?
• What are this leader’s goals? Do they have any goals or OKRs that are tied to this project?
• Has this leader’s leader confirmed that this work is a priority?
• Is this leader overloaded with multiple competing priorities?
• Has this leader confirmed they are aligned with the goals of the project?
• What have I already tried in order to better understand this leader and their concerns?
• Is there a different way that I could approach working with this leader that might be more effective?
• Have I addressed the issue with this leader directly?

I don’t have this list of questions written down. I don’t go through them in this exact order. I probably don’t even go through the entire list every time.

But over time, I’ve developed that list of questions to ask myself in order to problem-solve the issue. My experience has taught me that when there is a stakeholder issue, there are typically only a handful of root causes.

The questions are meant to probe at the potential root causes:

• Motivation. If this leader has conflicting or unclear priorities, it will impact their ability to work constructively on the project. If they are reluctant or not incentivized to change, they probably won’t.
• Bandwidth. They could be very supportive of the project, but if they are already over-committed, they won’t be able to actively contribute.
• Communication & buy-in. Maybe they don’t fully understand or agree with the premise of the project. Maybe they are aligned conceptually, but feel that their input wasn’t heard. Maybe they don’t feel this project will solve the problem. Either way, they aren’t fully invested.

The answer to “What do I do?” is based on which root cause it is. The action that I would take should address the specific disconnect.

Because I am equipped with a list of probing questions, I can begin to pinpoint the root cause. And because I have an understanding of those root causes, I know which actions I can take to begin to address the issue.

Now, I’m sure some people would do it differently. I’m not saying that my approach is the gold standard.

But when I deconstruct my thought process, this is what it looks like. This breaks down the steps to how I come up with an answer to “What do I do?” in a matter of seconds when my team member asks me.

It’s sort of like a magician revealing a magic trick. It seems complex and impossible from the outside. But once you learn the trick behind it, it’s actually quite simple. The secret is just in doing it quickly and smoothly.

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Teach the skills

The reality is, knowing what to do in certain situations isn’t actually a magic trick. It comes from experience and practice and the opportunity to learn.

The most effective way to get experience, of course, is to just try something, hands-on directly in your work. But some skills and situations are more delicate, and it would be risky to be trying a skill for the first time.

There are a few other really effective ways to teach skills to your team members:

Shadowing. Give your team an opportunity to see you in action. Where possible, let them sit in on meetings or workshops where you are using these skills. If it’s not possible for them to sit in, you can provide a debrief afterwards where you walk them through how you handled the situations that came up and let them ask questions.

Coaching. When they bring a scenario to you, and ask you, “What do I do?”, don’t give them the answer. In fact, don’t even assume that you know the answer. Stay curious and ask open-ended questions to help them uncover an answer themselves. Help them slow down their own thought process to ensure they’re thinking it all through.

Frameworks. Sometimes a cheat sheet or one-pager can be a helpful learning tool. The questions and root causes that I listed in the previous section? Those can be documented for team members to refer to over time. I always love a methodology — simple documentation is a great enabler.

Skills Training. It’s so important to keep your team continuously learning through team training. I particularly love role play exercises. For the “how to deal with a challenging stakeholder” topic, I created some example scenarios of various stakeholder challenges and each person took turns brainstorming how best to approach it.

Sample skills training for Challenging Stakeholder topic

Provide the opportunity

Look for as many opportunities as you can to let them practice their new skills. After all, experience is the best teacher!

A few opportunities to consider:

• Low-stakes situations. It might be intimidating (and ill-advised) to practice new skills for the first time with a big group of VPs. But there might be an upcoming presentation to their peers, or a meeting with a leader they’ve worked with in the past. Keep an eye out for safer practice opportunities.
• Stretch assignments. You should start low-stakes, but you can’t avoid that group of VPs forever. Once your team member has had some practice and proven to have a grasp of the topic, give them a more challenging situation. Plan to coach them and provide support as they prepare and debrief with them on how it goes.
• Coverage for you. When you’re out of the office, someone has to play the role of you, handling escalations and more challenging situations. Why not offer that opportunity to one of your senior team members? (Bonus: If it goes well, you can take more PTO!)

Conclusion

Don’t worry, your job isn’t going to be at risk. Your team isn’t going to learn to do everything that you do overnight. And their role might not require that they ever do.

But there are significant benefits to upleveling your team. Your team members will feel challenged and have the opportunity to grow. And you will be able to delegate more to them and feel confident in their ability to perform well with less oversight.

So don’t be afraid to reveal your magic trick!