8

Go Back in Time

Ask Past Colleagues about Your Leadership

MAKING YOURSELF INTO a more effective leader is hard work. You’re not going to make all the right moves, all the time. Wait, we have established that you’re not perfect, right? There is something you need to be working on, yes? Well guess what, that “something” has probably been there for a long time. Sorry to break it to you, but just as your leadership strengths are enduring, so too are your development opportunities. C’mon—you’ve always known about this weakness, right? Look back at the leadership journey you created in Chapter 1. If you’re like most leaders, there are some persistent areas you still need to work on. Although you can learn new things and improve yourself as a leader, you’re also remarkably consistent in your behavior patterns; change doesn’t happen that easily. What is an opportunity for you today has probably never been the strongest part of your leadership game. It’s OK to confront it. The first step in developing yourself is admitting that you have to break out and take charge of this, now.

Seek Out Former Colleagues

If you’re serious about making a change, here’s an interesting way of confronting the depth and extent of your development challenge. Look back at your leadership history. You’ve probably managed quite a few people along the way; certainly, you’ve had a lot of peers and bosses. They all experienced your leadership a little differently, of course. What could you learn from them today if you called them up and asked for feedback about what it was like to work with you? How could their perspective (after having a few years to think about it) help you now? What stories could they tell that would still be true of your leadership style today? How hard can it be to call people from your past and ask them what you did well or could have done better?

Now before you say “there’s no way I’m doing that,” stop and think about this for a moment. This is an incredible opportunity. These are people that have experienced your leadership firsthand; people you impacted either positively or negatively (yikes—maybe this is scary!). Hopefully, they remember you fondly and benefited from your leadership. But who hasn’t had a few bumpy relationships as a leader? The answer is we all have. And distance and time can sometimes bring much-needed maturity and perspective to what it was like to work with you. If you make an effort to collect input from people you used to lead, you can add a historical perspective to your current feedback. How great is that?

I’ve done this on two occasions, right after I took a new job. Knowing it was still fresh in their minds, I called the team I’d just left and asked for their feedback on my leadership. What I learned surprised me a bit; some of the things I was sure I had done right were not mentioned at all, and some of my concerns turned out to be nonissues. Because of the circumstances, I was also able to ask for specific feedback on how I could get off to a fast start with my new team; their ideas were great, and really helped me to be successful more quickly. I was definitely glad I asked for their input.

If you’re willing to try this, seek out five people from your past to interview about your leadership. At least three of these interviews ought to be with people who worked directly for you; peers or other colleagues can round out the feedback. Have these conversations in person or on the phone—don’t do this via email. It may be that you haven’t talked to some of these people in years; don’t be intimidated by that! Yes, you might need to find them, set up the concept, and arrange the call. But if you’ve kept in touch with the people that helped you throughout your career, you should easily be able round up five people to call to have this conversation. Now, what do you ask them?

Ask Three Questions

The easiest way to complete this exercise is to keep it simple. First, tell them what you’re doing, and ask them if they’ll take this trip down memory lane with you. Be clear that you’re trying to connect your past strengths and opportunities to how you’re continuing to develop as a leader. If the past relationship was particularly good, prepare to be dazzled by your own leadership brilliance (be modest when accepting their endless praise). If you have the courage to call a former colleague where the relationship was a little rocky, start out by acknowledging that you know you weren’t always the best manager. Show that you have at least some self-awareness about their experience working for you (this will set the tone that you’re open to listening to their feedback, and it will keep them from hanging up before you even get started!).

Begin by asking: “When you worked for (or with) me, what did I do really well as a leader?” Focus them on your strengths first. Let them talk freely about your leadership style, but try to get specific about your core competencies—what specifically did you do that worked for them? Next, ask them: “What did I do that frustrated you or made your job harder?” In other words, ask, “Where could I have been more effective as a leader?” Asking where you fell short in this way makes it real for them. Rather than asking them to simply recall your weaknesses, you will be asking in a way that will stir some tangible memories and allow them to tell you what it really felt like when you weren’t at your best (I know, you’re freaking out again; but stay with this—be brave, you can do it!). Finally, ask this question: “Overall, what did you learn working for (or with) me?” Ask about your lasting impact—your leadership legacy. Good or bad, you probably made an impression in their lives and career; find out what it was. This can be the most profound (and rewarding) lesson you’ll take away from this exercise. After all, although you may not be able to make a difference in their lives anymore, you certainly can impact your current and future employees. Get a sense of how your leadership shapes people long after you’ve stopped working with them.

If you really want to take stock of how far you’ve come as a leader, you need to take a trip back in time and check in with former colleagues. Reaching back into your past helps you identify consistent leadership strengths and opportunities and shines the light on your development progress. Hopefully, you still have all of the good leadership qualities they liked about you, and you’ve made significant strides in the areas that they remembered as weak. At the very least, you will have reconnected with some old friends and co-workers. Talking about what it was like to work for you, even years later, can be humbling and scary. It can also be incredibly productive and feel really good. No matter what you’re expecting, you’ll probably experience a little bit of both. Trust me, it’s worth the effort.

Bootstrap Takeaways

Ask Past Colleagues about Your Leadership

1. Ask former direct reports and peers what it was like to work with you. Tap into their perspectives, which have aged and matured with time.

2. Reach out to people you know enjoyed working for you as well as a few who struggled with your management. Get a balanced view of your leadership style.

3. Be humble, gracious, and appreciative. Thank them for their feedback, and weave it into your continuing efforts to improve your leadership skills.