Orchestrating Leaders

CONVERSATIONS WITH THE BOSS

Here are some sample conversations some of you may be able to relate to.

Conversation 1:

My boss: “Okay. I know last year we held an event to make emergency meals for 10,000 people. This year, we’re going to make meals for at least 100,000 people.”

My brain: “This is crazy. We have about 50 more people than we did last year. How on Earth are we going to pack 10 times the number of meals we did last year, let alone afford it?”

My mouth: “That sounds awesome. I’ll get to work on figuring out some of the ‘how’ pieces.”

Conversation 2:

My boss: “We’re going to put on an officially timed 5K in Annapolis to raise money and awareness for food insecurity in our county.”

My brain: “We? We are doing this? I have a bachelor’s degree in Geology, an MBA focused on organizational design, and 18 years of playing bass guitar on my resume. I’ve only even been to one or two 5Ks, and they were all turkey-themed.”

My mouth: “That sounds awesome. Who do you think I should loop in to help sort it out?”

These conversations happened nearly a decade ago, but I can still remember the smell of dry-erase markers that always permeated my boss, Josh’s office. I remember my brain shifting to race gear as it surged down pathways of planning and contingency. I could feel the stress and maybe a hint of panic. Literally. It was manifesting as drops of sweat sliding down my back.

For nearly 20 years, I have been in leadership positions, but I have never been THE leader. I have always had a boss whose role consists of casting vision and setting direction because their strengths lie in seeing the future and integrating their imagination into it.

My job has been to turn that vision and direction into a reality because my strengths lie in being able to see how different pieces do (or don’t) fit together and identifying the new patterns or new pieces needed to accomplish the vision.

Leading while also being someone else’s subordinate is challenging, but it can be one of the most rewarding positions in an organization.

Some people who are in roles like this are on a journey to being THE leader, and others, like me, look for roles like this. Whatever the case may be, communication is essential to success and fulfillment.

COMMUNICATING & LEADING UP

Being good at one thing sometimes comes with consequences.

I’ve been playing bass and guitar for over 25 years and the fingertips on my left hand have become thick, unfeeling callouses. This is true in leadership, too. Visionary leaders who are focused on what could be rarely stop to think about the problems that will be created if the organization chases their vision. Orchestrating leaders, like me, who are focused on “the how” get so focused on the problems that they fail to see the beauty of what could be.

Effective communication is the best way to help these seemingly opposing positions coalesce into an impactful collaboration.

Since my experience has been as the leader who has a leader, which I’ll call an orchestrating leader, I’m going to share tips from that perspective:

1. Lead with an enthusiastic “Yes!”

The quickest way to suck the energy from a visionary leader is to say “no.” I remember having a vision for making my kids eat broccoli, asparagus, and a variety of other vegetables at every meal. After a million no’s, that vision has been replaced with a contentment with them eating anything that isn’t breaded or drowned in cheese. The word “no” is immensely powerful.

 You may be saying, “If I say ‘yes’ to everything my leader says, our organization is going to come apart at the seams.” If only the word “yes” was as powerful as “no.” When you say “yes” to your leader, it doesn’t have to be a commitment to the ending they’ve envisioned. Your “yes” is a commitment to stepping toward that ending.  Your “yes” is saying you hear the potential in their vision and are willing to trade the comfort of status quo to take a step toward it.

 Communication is bidirectional (at least) and the best communicators ensure the audience they are communicating with knows they are heard. When you say “yes” to a visionary leader, it tells them that you heard them and you understand the potential. When you say “no,” you tell the leader you checked out at the sight of a problem and didn’t absorb the potential.

 Last thing on this point. Make your “yes” enthusiastic. The leader you’re working with is excited about the potential. You can be, too. Most leaders are pretty smart. An unenthusiastic “yes” is only marginally better than a “no.”

2. Catalog questions, not concerns.

When my wife and I bought our house in 2018, we had a home inspection done. Our house was built in the 80s and had already played host to a generation of rambunctious kids. We were not expecting a clean bill of health. What we received was a notebook with descriptions and pictures of every problem in the house. It was pages long. I had to read it in chunks because it was really stressful. Are we buying a money pit? Is this thing just gonna fall down around us? Fortunately, I had some friends who had recently bought homes with some age on them that asked me questions about the inspection report.

 Them: “How important is it that there is a door to nowhere on the back of your house?”

Me: “Not that important, we can build a deck in the next year or two.”

 Them: “How important is it that your windows are a little drafty?”

 Me: “Well, they still lock, and they’re not so drafty that the HVAC can’t keep up, and we’ll probably replace them anyway.”

 Them: “How important is it that they found some Radon in the basement?”

 Me: “That’s super important. I don’t want me or my family to be at a higher risk of lung cancer.”

 Them: “Okay, so out of the three things we listed, only one of them is urgent?”

 The binder of issues to deal with was overwhelming. It sapped my energy and made it impossible to see all the amazing things about our potential future in the house: the great schools, the proximity to water, the amazing community events we could walk to, not to mention the ice cream shop.

When the catalog of concerns was put into question format, it helped me see that there was still a path forward, albeit with some repairs and a huge air pump thing in my basement.

 When you say “yes” and move in the direction of the vision that has been presented to you, you will encounter problems. That’s inevitable. Try to address them, then come up with questions you can ask.

In the first example above with the event to pack meals, I was able to ask, “How important is this to finish in three hours like last year?” and, “I think we are going to need about 100 people beyond what I can project from what I know right now. Is it cool if we collaborate with some other organizations in the area, or should we work on figuring out how to drive this on our own?”

 We extended the event to nearly nine hours and collaborated with several partners in the area. That wasn’t the original plan, but we still accomplished the original vision (plus about 10,000 extra meals).

 Asking questions will help clarify your path forward and demonstrate that you’ve put thought into it while helping to mitigate the sense of overwhelm that a list of problems would probably impart. The questions may lead to an adjustment and occasionally may reveal an insurmountable problem, but they will always lead to collaboration and trust building.

 Quick side note with a healthy dose of side eye: We all know there is a way to ask questions that are intended to overwhelm the person being asked. That’s not what I’m talking about here.

3. Celebrate.

Orchestrating leaders often suck at celebration. By the time one thing is done, I’m already working on the five next big ideas I’ve said “yes” to. If I’m really firing on all cylinders, the accomplishment of one idea is indistinguishable from a phase in the accomplishment of another idea. It’s all meshed together in an effort to take out multiple birds with a single stone as the saying says.

But celebration is important. My boss had a cool idea, and we did something with it. An idea’s value is born out of its implementation, and we did it. An idea turned into a thing. It was an itchy caterpillar for a while, then an ugly cocoon for a bit, but it emerged with wings.

That’s cool.

That’s worth celebrating, and celebration reminds us of how our roles complement each other. And that reminder helps us get better and better as we do it again and again.

Matt Murphy - VP, Stadia

Matt has an MBA from the University of Maryland and uses his experience to coach leaders of non-profit organizations in his spare time.