Part 1: Why Having A Wingperson Matters

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What is a Wingperson?

I’ve always had someone on my team who I have called my wingman or wingwoman. I credit a lot of my overall career success in having the right people at my side to support, guide and challenge me. Some of the most intense, thoughtful discussions I’ve had at work have been with my wingperson. In return they provided me unfiltered feedback that helped me grow as a leader and person. There’s a reason that kind of relationship is hard to have at work, but the value of having one far exceeds the difficulty in finding one.

First let’s describe what I’m even talking about when I say wingperson (WP). Ideally he or she is someone you trust and can have an honest, transparent relationship with. They have the ability to keep your conversations private, allowing for open discussions about the lay of the land at the company you work for. They can often be your “go to” for important tasks or projects, and they ultimately support your vision. She or he needs to be as invested in your success as you are in theirs. It doesn’t work without skin in the game for both parties. Obviously you have to do work to get them engaged with your vision, but the point is this is a two-way relationship. All of this goes back to the main requirements of a WP: trust, honesty, and transparency.

Having a WP is often critical to your career. Certainly having a team of people supporting you is good and no business works without that dynamic. But, the value of a WP is about having a partner who is along for the ride and aligns with your goals. Someone who wants to see you succeed and the feeling is mutual. A WP is the one who tells you that you ran a shitty meeting without focus or purpose. They are the person who brainstorms with you. They are the one who can tell you your ideas suck or are amazing. They keep it real. They bring optimism to your pessimism and vice versa.

However, a WP is NOT your personal assistant¹. This isn’t to knock on people who are personal assistants, they are some of the hardest working people out there. It’s just that a personal assistant is invested in your success in a different way. Certainly a personal assistant could be a WP, but it isn’t the first place you should look. Think of a WP as an advisor who often reports to you (not required), but someone who still operates independently of you.

For me, I’ve been fortunate to have a few trusted advisors in my career that would qualify as a WP. It is interesting, because without exception, I’m still in contact with those people. I still trust their advice and I call all of them personal friends. So having a WP is not just a business relationship, it’s a lasting, personal one.

How do I find and establish a Wingperson?

Historically, for me, they have always been one level below me, usually in a leadership position themselves. There is complexity to going this route, but I’ve had the best luck with people who have reported to me directly. It makes sense in that they are near the work I do and are often interested in learning more about the work. They are always curious and they never say, “This isn’t in my job description”. If I hear that statement, I run in the opposite direction as fast as my feet will take me. I’m looking for someone who understands that work is more than lines in a job spec. They don’t have to be corporate ladder climbers, but having ambition is a good behavior to seek. Ideally they want to do your job in the future (so you have an obvious succession plan). If they are smarter than you, even better.

With all of this being said, selecting your WP isn’t as easy as waving a magic wand and saying, “I deem you my WP and it’ll be amazing!” It’s a process that should be slow and ultimately obvious. I start with having regular meetings or one-on-one sessions with the person I think would be an ideal WP. I share direct feedback and I engage them in brainstorming conversations. I ask them to provide me feedback on my performance, noting if they can give me constructive, honest feedback. In reality, this person is often someone you could see taking your job in the future. Having a good WP isn’t mutually exclusive from having a good succession plan that involves the same person.

If you go with a WP who reports to you, there are dynamics to consider². If you have 10 people reporting to you, all at the same level, how do you elevate one person while not demotivating the rest of the group? One option to consider is to offer a senior role. For example, you may want to promote someone into a senior position so they can have additional responsibilities, career growth and acknowledgement. This allows you to build a unique relationship with that person without harming team dynamic. Above all else, remember what is most important (more than having a WP): your team’s engagement with you and the company. If you treat everyone fairly, and if you have chosen the right WP, people will understand that decision.

Another option is to look for a peer in another department that has some cross-over with your work and team. I’ve had one wingwoman and wingman in my career that was a peer and did not report to me directly. The requirements are the same: trust, honesty and transparency. Having a WP like this has some benefits in that there isn’t a boss/employee dynamic, and you can get a really solid outsider perspective that might be missing from someone on your own team.

Assuming you have identified the person who is your WP, you should have a conversation with them about what kind of work relationship you want with them. If they report to you, I would explain that you are looking for someone who could ultimately do your job. More importantly you are looking for someone to bounce ideas off of and someone who can push back on the extra crazy ideas. You want their feedback, more than anything. Establishing the way you want to communicate up front is critical because you’re going to want to immediately start having those open, transparent conversations with each other.

What does having a Wingperson look like in practice?

Isn’t it just a glorified direct report or a peer you are friendly with? Fair question. For me, they are trusted advisors. It’s critical for me to make sure they know I’m invested in their success, in whatever they want to do. I’ve had advisors who told me up front what their career goals and plans were. Not always did they involve the work they were doing, but I committed to doing everything I could to help them with their goals. Even if it meant they would leave. You have to put it all on the line. This is why I’ve ended up with life long friends who were my WP…we genuinely cared about each other³.

Here are some examples of what it looks like having a successful WP:

• You just did a big presentation to the entire department about improving productivity. The WP tells you afterward that people were not pleased with the message you delivered. They explain how you can adjust your message to get the same outcome.
• You’re coming up with a new program that will improve overall quality. Before you share it with your boss, you need someone to poke holes in your proposal. The WP will challenge you and ask hard questions that will ultimately improve the program proposal.
• Your WP sees you aren’t being assertive enough in a cross-functional team meeting. They point out that you should be pushing harder to get the best outcome.

What experiences have you had with having a WP? What are some of the triumphs and pitfalls? Leave your feedback in the comments!

Up Next: Why BEING a Wingperson Matters

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Footnotes
¹ 99% of us do not have a personal assistant, so I recognize this problem is nonexistent for most people. I just want to call out that having a personal assistant isn’t an automatic “wingperson” scenario.
² There is always complexity and risk to having your WP report to you directly. Yes, you could have someone that operates as a WP who gets into a performance issue. Before you select a WP, you should spend time thinking about how you would tell them they were not performing, because if you think they’d not handle it well, that’s a warning sign to not proceed. In theory, if you have to terminate a WP, the relationship lasts because you’ve always had honest conversations with each other. I’ve been lucky, this hasn’t happened. This is not different than having a good friend who reports to you, which is a common workplace situation and has almost identical complexity. In short, be careful and do what’s right for the person.
³ Having a WP isn’t for everyone! If the idea of caring for an employee or peer at work sounds impossible to you, don’t do it. I’ve seen people try to fake empathy with their employees. It fails because it becomes obvious. You are either genuine or you are not. People pick up on that a thousand miles away.