Shadowing: Your Surprise Secret Weapon for Leadership Success

Help your team members step up by letting them “shadow” you in your job. This shows them how you spend your day, what you do, how you do it, what problems you face, and how you manage difficult situations. It also gives them the chance to ask relevant questions, which helps you understand and assess their current knowledge.

One of the biggest benefits of shadowing is that the learning is highly relevant. Your team member learns from real situations, they learn directly from you, they are exposed to complex situations in a safe way, and they only ask questions to fill a knowledge gap.

However, if you’re not careful, it’s easy for this learning environment to be too informal, where you both just go through the motions without any real learning. This usually doesn’t happen intentionally; it’s just the natural consequence of a busy working life.

To prevent this problem, add some structure to the shadowing process, to hold you both accountable to the learning process. One of the easiest and most effective tools for this is debriefing.

A debrief is simply a structured review of an event. Debriefing is common in some industries – for example, an airline flight crew debriefing after a flight or a hospital operating theatre team debriefing after a complex operation. Even if you’re not flying a commercial aircraft or conducting open heart surgery, you can still get the benefits of debriefing, which has been shown to improve both individual and team performance .

For example, if you take your team member to a management meeting, you debrief them afterwards by discussing the content (what was discussed at the meeting) and the process (how the meeting was run).

Debriefing a team member shadowing you can be even more effective than a team debrief, because it’s a positive and open discussion (without the potential to be negative or critical, as can sometimes happen with team debriefing).

In his book Work Rules!, Google’s Senior Vice President of People Operations, Laszlo Bock, describes how a former manager used exactly this process to accelerate Bock’s experience. He and his manager, Frank Wagner, drove out to client meetings together and Wagner debriefed the meeting immediately afterwards on the drive back to the office. The debriefing was simply asking Bock questions like “What did you learn?” and “What do you want to try differently next time?”

Let’s look at the debriefing process using a specific example of you inviting a team member to accompany you to a management meeting.


Although we focus on the debrief, which is about what happens after the meeting, you can also brief your team member beforehand. This isn’t essential, but it can help in certain situations – for example, to explain the dynamics of a group, to suggest they observe something particularly carefully, or to alert them that you’re planning to call on them during the meeting.

Make it efficient

Ask them to take notes about what they observe and any questions they would like to ask you later. Resist the temptation to ask them to take your notes for you, because this is for their benefit, not for them to act as your personal assistant.

When the meeting is complete, make time for debriefing – and do it as soon as possible, while it’s fresh in your minds. If you leave it too long, you will only remember the most prominent things, and might forget something subtle but equally important.

Debrief process and content

Most discussion after a meeting tends to focus on the content (what was discussed). When debriefing, also make time to discuss the process (how the meeting was conducted). Your team member will learn from both, but will probably learn more from the process.

For example, in a management meeting about recruiting a new staff member:

  • The content might include the role requirements, salary, and headcount restrictions.
  • The process might include unspoken assumptions, hidden agendas, the chairperson’s role in managing the discussion, and the way people stated their opinions.

Discussing the content helps them understand that particular issue; discussing the process gives them a broader perspective about meeting dynamics, office politics, decision making, long-term strategy, budgets, and more.

Ask first

It’s tempting to treat debriefing as an opportunity for you to “share your greater wisdom” with your team member. However, you will gain more by asking first for their input and taking the time to listen. This encourages them to be assertive, allows them to express their ideas, lets you choose which issues to address, and helps you understand their level of understanding.

If you’re doing this for the first time with a team member, they might find it difficult to share their ideas. In that case, prompt them to share by asking questions. For example, you could use the What / So what / Now what structure, which goes like this:

  • What? What did they notice (for example, “Jamie looked nervous talking about the new person’s salary”)?
  • So what? Why do they think that happened (“Maybe her project is going to have a budget blow-out”)?
  • Now what? What could happen next, or what do they suggest as possible next steps (“Perhaps we should have a private conversation with her, because that could affect our budget as well”)?

Share your expertise

Your team member won’t always identify everything important, so it’s your responsibility to identify other things worth discussing. You can use the same What / So what / Now what structure to frame your thoughts.

Be prepared to justify what you say – and in fact, encourage your team member to ask “Why?” frequently. At first, this might sound like a small child repeatedly crying “But why?” However, it can be very useful for both of you (as long as you don’t end up saying “Because I said so – that’s why!”).

For example, if it was you who suggested the private conversation with Jamie, your team member could ask “Why?” to understand:


You: “Because it’s better to know about her problem now than wait for next month’s meeting – which might be too late.”


You: “Because the next three weeks are critical for us, and we can’t afford any delays.”


You: “Because we need to send Paul the widget design by the 15th, and if that’s delayed, everything down the track is delayed, all the way up to the launch in November.”

By digging deeper using “Why” questions, the team member understands the real reasons behind your thinking.

Look forward

Another benefit of digging deeper with “Why” questions is that sometimes your team member suggests options you hadn’t considered. In fact, a very valuable feature of debriefing is that you get to “bounce your ideas” off somebody else, and the fact that it’s somebody less experienced doesn’t make the process any less valuable.

As your team members become more familiar with the process, you can – and should – ask for their advice as well. They will often contribute valuable ideas, opinions and perspectives.

Debrief the debrief

There is no ideal way to conduct a debrief, and different people will do it differently. For example, one team member might be happy to do it immediately after a meeting, while somebody else might prefer to reflect for an hour.

Start with whatever seems best for you, and later (when they become more familiar with the process) ask them for suggestions to improve the process.

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