Leading Up: How to Impress and Influence Your Boss

Part III in a 3-part series.  If you missed the other posts, start here

Monkeys in a tree. This may be familiar to you but I had not heard this analogy before this week.  I was sitting down with a business leader over coffee and he explained to me that when you’re a monkey in a tree and you look down, you see smiling faces looking up at you, but when you look up, well, let’s just say the view is quite a bit less flattering.

I wish there wasn’t any truth in this analogy. Unfortunately, it is easier to see the faults of those who lead you directly than just about any other person in the organization.  Mostly, I think, because their bad decisions can affect you so much more heavily. If I were to name one dynamic that most often sours relationships with bosses, this would be it.

If we’re going to lead positive change in our organizations, we need to curb our criticism and learn to cultivate influence instead. Whether or not your boss will admit it, they need your help to lead well, but they’ll never accept it from you unless you first learn to build trust with them.

Series Recap

If you’re just jumping into this 3-part series now, we’re discussing why it’s not enough to simply lead out of your official positions of authority. In order for you to add the most value possible to your organization, you need to have an influence across all layers of leadership.

What you can do with authority is limited, what you can accomplish with influence is immeasurable.

Authority gives you the power to change short-term outcomes; influence gives you the power to change culture.

This is especially encouraging for all of you out there that don’t have the position or the title yet. It means you have the ability to significantly move your church or organization forward in its mission regardless of where you are on the Org chart.

We’ve already covered what it looks like to influence those we lead and those we lead alongside, but now let’s shift gears and talk about how to have a voice with those who lead us. Here a just a few principles I’ve learned that will help you impress and influence your boss:

1. Care about what they care about.

Your boss has to lead at a different level than you do, think through challenges that you don’t have to, and plan farther into the future than you do.  They care about what you do but are more concerned with how it fits into the bigger picture and aligns with the overall strategy of the organization.

This is good.  They need to do this. We may get frustrated when they don’t seem to really understand what we do or ask us to do something that is far more work than they realize, but it’s because they need to be leading at a higher plane than we are.

Instead of fighting against this, embrace it and help them accomplish what they are responsible for.  Prove that you care more about the future and success of the church than you do about getting that budget increase this year and you’ll go a long way towards gaining their trust.

You want a simple way to prove that you care about what they do? Next time they bring forward a church-wide or staff-wide initiative and need to form an ad hoc team to accomplish it, be the first to raise your hand.

Key Question: “If I were to let my boss re-prioritize my calendar, what would it look like?”  

2. Be low maintenance.

Regardless of what your position is or what task you’ve been given to do, figure out how to do it better than anyone else.  It doesn’t matter if you’re an intern working the copy machine or leading a team through a major new initiative, be the one that your boss never needs to worry about.  They know you’re going to get it done and get it done well.  In the midst of high pressure or stressful seasons, you need to be, as Clay Scroggins puts it, “an oasis of excellence” in your organization.  Don’t be a burden.

This seems like it should be obvious advice – work hard – but it’s amazing how quickly a proper work ethic can set you apart.  Do NOT fake this, though. If something really isn’t working well in your area of responsibility, don’t create the illusion that it is.  You don’t have to be perfect, but you do have to be honest.

If you want to gauge how you’re doing in becoming this “oasis”, Scroggins recommends this key question:

Key Question: “What would my boss’ gut reaction be if they found out I was resigning?” 

3. Learn how to disagree with them.

Ok, take it easy on this one, no one really wants to work with someone who is constantly the dissenting voice.  But the opposite is also true. I don’t need my team to always agree with me; I need them to be effective.

If we’re going to see the right ideas come to the surface, we need to develop the art of the “pushback”. Respectfully, and with humility, provide some opposition and ask some tough questions. No leader has all the answers or is thinking about all the angles; the best leaders out there are the best because they’re surrounded by the best teams.

Our churches don’t need charismatic, rock-star, pastors calling all the shots; they need healthy teams of leaders who are willing to wrestle their way to truth and discern together where God is leading them.

The key to gaining influence through this is to learn to disagree with them while still continuing to honour them as your leader (I.e. this is not a license to criticise them behind their back).  If your boss can trust you to be honest with them in private, while honouring them in public, you’ll become invaluable to them. Not only to them but to your entire church/organization as well.

Key Question: “When I see something that I disagree with, how would you like me to approach you?”

4. Grow.

Don’t be a static member of the team. The need today is for dynamic leaders who are constantly learning, adapting to changing cultures, and not afraid to innovate. Be intentional in carving out time regularly for your own leadership development.

While your boss should be encouraging and equipping you to do this, not all of them do; in the end, your growth is always your responsibility.  Prioritize this and you’ll find it far easier, and more natural, to be the one who is bringing new perspectives and fresh ideas to the table.

If you really want to grab their attention, take some books from their reading list and add them to your own.  Find out what books have influenced them the most in the last year and then pick up a copy (or borrow theirs to see what they’ve highlighted and underlined).

Apart from books, consider other avenues of growth like getting a coach, taking online courses, joining a mastermind group, or attending conferences. Whatever you do, just do something.  Don’t rely on your degree from 2008 to effectively lead the church in 2018.

Key Question: “What books would you add to my reading list this year?”

Next Steps

There are so many other ways that you can build trust and learn to influence your boss.  These 4 questions are a starting place; now it’s up to you to get to know your supervisor personally and adjust your strategy accordingly.

I’d love it if you shared your ideas with us in the comments below.

Whatever you do next, I hope you have a new appreciation for your ability to Lead from the Middle.  You don’t need the authority that comes from position or title.  You are perfectly situated to lead change in your church/organization right now, regardless of what the sign on your door says (or even if you have a door).

If you’ve appreciated this series and would like to download a PDF of all 3 articles, along with a one-page overview of the 11 key questions that we’ve suggested, simply fill out the form below and I’ll make sure to email you a copy!

-Dan