20 Lessons from 20 Years of Leadership Coaching - Part One

This past February, our company hit a milestone - we have supported leaders and teams to work together better for two decades. And to celebrate, we are sharing the Top 20 lessons we have learned along the way in a two-part series.

We hope these reinforce what you have learned on your leadership journey, or perhaps provide another perspective to consider. To make this list not quite so overwhelming, here are the first ten lessons, focusing on what we’ve learned about organizations and leaders:

Organizations

1. Organizations will go as far as their leader is willing to grow and let go

You and every leader are great at some things, not so much at others. One of the hardest challenges for you as a leader is to let go of doing something you’re fantastic at so someone else can do it. The next hardest challenge is to look hard at yourself and unlearn what’s not serving you or others, and then grow into a new way of operating.

2. Most people think in terms of next steps - raise their sights to the outcome instead

When working through a problem, most people focus on the next few steps. While helpful, the real opportunity is to flash your high beams down the road to the outcome we all need. Whether it’s just one person or a whole team, getting everyone to focus on the needed outcomes can provide the context for what next steps will be most helpful.

3. Most of the opportunities in organizations are between the functions

People are usually quite good at seeing needs, making decisions, and taking responsibility for their own discipline, function, or portion of the organization. The places we fall short are between the functions - opportunities to improve organizational effectiveness, meet emerging customer needs, or even growing leaders who aren’t just one-trick ponies from climbing a singular functional ladder. (Ok, mixed metaphor but I think you see the opportunities lie in the spaces between where your organization is already excellent.)

4. Asking “What does the business need?” can dramatically improve the organization.

Optimizing individual components of an organization automatically de-optimizes the whole organization. If sales sells three times the number of clients you can support, or operations produces three times the forecast, or worse still, one function “wins” over another, in actuality everyone loses. Instead, if everyone asked about and focused on the overall organizational need first, you can share ideas, resources, and get to the finish line together.

5. To get commitment, make sure everyone’s crayon is in the picture of the future

Jack Stack, co-author with Bo Burlingham of The Great Game of Business book, says “People support what they help create.” If people are listened to and their ideas are understood and considered, they have ownership of the end result and the work required to get there. We often facilitate organizational planning efforts where leadership teams come in believing the needed result is a perfect plan, and realize part way through that creating an imperfect draft with opportunities for input and improvement is less pressure. This better supports everyone’s shared ownership of the results. If a person can see even one pixel from their crayon in the overall picture, they will have pride in their authorship.

Leaders

6. Leadership is a choice not a title

Many people believe that you need a leadership title to be a leader - that leadership equals formal authority. It’s actually the other way around. The best way people can get a leadership title is to lead by example. Serve the mission and the people, contribute to making the organization better, improve yourself, and you will be a leader.

7. One of the most powerful choices you can make as a leader is how you choose to show up every day

Leadership is much more caught than taught. It’s not what you say, it’s what you do that matters. Too many leaders are unaware of the impact of how they show up. To transform yourself and your organization, get and then act on direct feedback of what you’re doing well, what you’re not doing well yet, and what’s missing or unclear. Spoiler alert: you’re having an impact right now - what do you want it to be?

8. Asking “How can I help?” if not as helpful as you might think

To answer this question, the person you ask has to do multiple things: diagnose what’s not going well, prescribe what could help it be better, assess your ability to provide the prescription, and then decide whether asking for that will diminish your belief in them. While people can find answers to these questions, it’s a big burden to someone already struggling. Instead, try working from the diagnosis up:

  • Where are you having challenges?

  • What have you tried?

  • Here are a couple of things I could do - which would you like?

  • Thanks for allowing me to support you so we can get what the organization needs.

9. Give people permission to bring out their best

My coach, the late Richard Reardon, used to ask me these questions when I was struggling:

- “I know you don’t know, and if you did, what would it be?”

- “If you could wave a magic wand, what would great look like?”

Leaders occupy a unique role in creating the space and opportunity for people to grow beyond their current reality. It is amazing what people find they know and can do when someone believes in them.

10. Instead of asking “Why?” ask “Imagine you have just what you need - what’s different as a result?”

Asking “why?” five times in a row is a powerful method to get to the root cause of a challenge or problem. In practice, this line of questioning can cause people to become defensive and less open to (your) outside influence. Instead, give people permission to have exactly the change they are looking for and ask what’s different. Keep doing this until you both discover the real reason for the request - the invisible intended outcome - which will help you and them both decide how to proceed.

Which of these lessons resonate with you as a leader, and which could be helpful to explore in further depth? Let’s set up a conversation to see what could be possible for you and your team. And stay tuned next month for the rest of the list.