Part 2: Why Being A Wingperson Matters

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To give is to receive

In my previous article, Why Having A Wingperson Matters, I talked about what a wingperson looks like (I would strongly recommend you read that article first if you haven’t):

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…All of this goes back to the main requirements of a wingperson: trust, honesty, and transparency.

Obviously being a wingperson (WP) will help you appreciate the value of having one, but the biggest reason to be a WP is that helping others is one of humanity’s great callings. Being able to help a manager or leader is one way to join forces for the good of both. It may be the truest form of teamwork in that it’s a binary relationship that requires both parties to invest. In all the situations where I’ve been a WP, the most rewarding part of the experience has been how we became friends and supporters of each other¹. I’m not saying that being a WP to someone will get you a BFF, but I am saying that giving to others often leads to larger rewards as a human.

Deciding if your boss is worth the investment

Before going any further, you need to decide if you want to offer this type of support to your boss. Timing is important. For example, if you are being coached on your performance or you just recently started a new job, the time is not right. However, if you have a solid working relationship with your boss, that could be an ideal time to talk to them about ways you can partner (perhaps you start by sharing this very article!). The conversation should focus on your desire to support them and help them be successful, while also asking for that same level of support. The main requirements need to stay the same for both parties: trust, honesty and transparency.

I’d also go an extra step and make sure you establish with your boss the ways in which you hope to support each other. Having this conversation up front is key, since “help” can be defined in a lot of different ways. It could be helping on projects, taking on new tasks to provide relief, or learning new skills to support their growth. I’ve been a virtual Chief of Staff to a few of my bosses, helping them think through strategy, challenging them on their proposals (respectfully) and assisting them in communicating their ideas to the larger organization. I didn’t serve in that support role, though, until I established how I hoped to support them in their own career.

There’s also a good argument to make that you could also offer to be your boss’s WP when you don’t have the best relationship. First, you would need to establish if they were receptive to the offer. Have a conversation where you explain that you want to help them be successful, and find out what their career or job objectives are. Knowing where they want to go will help you know how to help. I can’t think of any situation where your boss would not appreciate the conversation, even if they aren’t interested in having a WP².

Learn the role, learn the business

There’s a practical element here, of course, which is that being a WP can be an excellent opportunity to learn more about the business and your boss’s role and responsibilities. While you should never end up as a de facto personal assistant, there is value in learning about the details of their job. Even if you aren’t interested in moving into their position at a later date (when they’ve been promoted thanks to your amazing support!), understanding the business and how your role and their role fit into the organization is worthwhile. When your boss is out of the office on vacation, for example, you can answer questions and potentially do some of the work so that when they return you are both the hero and establishing yourself as a “go-to” when they aren’t around.

The other reason it’s a smart idea to learn the role and the business is that a WP often ends up as the ideal person to take over the role your boss fills when they move up or out of the organization. One of the most important jobs of any manager is to have a good succession plan in place for their team and themselves. Being that WP sets you up as an obvious person to move into that role. However, don’t assume it’s going to happen without you proving yourself to others. While your boss may be your biggest advocate, you need to put time into developing strong, positive work relationships with your coworkers and other leaders in the organization too.

Be aware of the risk

Some people will say that being a WP is too risky, too giving of your time and trust, and is opening yourself up to being taken advantage of by your boss. That is a valid concern! There is always risk, particularly if the relationship isn’t properly set up at the start. If you don’t have the trust, honesty and transparency from the start, it doesn’t show up later. If you aren’t talking regularly (daily even) with your boss and you aren’t receiving support from them, that is a warning sign. If, after discussing your concerns about the WP-setup not working, they do not change or aren’t receptive, stop immediately. Being a WP doesn’t work unless the relationship is beneficial to both of you, with a genuine desire with both parties to support the other³.

Having a partner in crime at work can lead to a lot of opportunities that might not exist if you didn’t invest the time to be a WP. As I’ve mentioned before, I’m in contact with and friends with many of the bosses that I’ve been a WP for because of the time we put into supporting each other. I wouldn’t trade those experiences for anything, both because it was a smart career strategy and it was satisfying to help someone besides myself.

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

Out of the Weeds Consulting’s mission is to provide immediate operational support, while getting you out of the daily minutiae to focus on what is important. Contact us here for a free session to find out how we can help.

Footnotes
¹ It is worth taking a moment to acknowledge that you aren’t perfect, and neither is your boss. We all have strengths and weaknesses, and the best way to start any work relationship is to acknowledge your own positives and negatives. In an ideal world, your boss can help balance out your weaknesses and vice versa. But even if that isn’t the case, humility with your own imperfection is the perfect place to start before deciding you want to be a WP.
² If you have a strained relationship with your boss, do not proceed. The type of relationship that I am describing is one that is cordial, but not necessarily engaged. I’ve had several managers that were so busy they didn’t have time to build the relationships they wanted with their employees. That is an IDEAL situation where you can help.
³ There are all sorts of flavors of risk too. For example, you may be such a good WP, your boss may not have incentive to see you grow. For example, if there is another position open in the company that you would be ideal for, if your boss isn’t advocating for you, that could be a sign of a problem. I know I keep repeating it, but the foundation of the relationship has to be trust, honesty and transparency. If you aren’t seeing the career support you’d expect from your boss to match the level of effort you are putting into their growth, stop immediately and reassess.