It’s Lonely At The Top

One of the most critical indications of leadership is when there is an issue or problem. If everyone looks to you, you’re the leader, even if you aren’t the boss or manager. And we call those problems you face as a leader that no one else can easily help solve: the “tricky problems” of leadership.

Get Started

Entry-level employee

Early in your career, your role was likely well defined, and the problems you faced were easy and relatively low risk. At the same time, you had lots of people to turn to for answers or help, including peers, a manager and other people above you who were there for answers. Often, there was someone there who just told you what to do in a given situation.

Senior Leader

As you demonstrated your potential and moved up, the problems got harder and more important, while the number of people you could turn to for help got smaller. Your peer group in the organization shrank and there were fewer and fewer people above, until one day, everyone was turning to you for help and answers.

A panel of experts to help you work through every tricky leadership problem you face

Our secret is increasing the number of people you can turn to for answers, accountability and support. It starts by matching you with an expert group of peers. These fellow leaders become your personal board of directors who will be there to help you work through your tricky problems.

Tricky problems are R.I.C.H.


You are the one who needs to resolve this, either because it’s your responsibility, your area of expertise, you feel responsible, there isn’t anyone else or some combination of these.


Getting this right really matters to you, your team, or even the entire company. This could be a key decision like whether to expand to a new market, how to handle a competitive threat or what the next step is in your career.


There are multiple interconnected parts to the problem, such as several people or organizations involved. This could be consolidating teams after an acquisition or figuring out how to manage a day job and a side hustle simultaneously.


You can’t solve this quickly because there are no easy or obvious answers—every potential path has tradeoffs. It is keeping you up at night.

Important vs Urgent

We’ve found it helpful to think of these tricky problems along two axes: importance and urgency.

Solve sessions

This process has been so valuable for our members, we’re expanding it beyond the group meeting sessions. We call this Sidebar Solve. This is an opportunity for community members to come together, outside their Personal Boards of Directors to leverage Sidebar’s signature problem-solving methodology on a drop-in basis. Members may join a Solve session to work through an urgent problem, to be of service to others in the community or simply to learn.

Start Solving

Sign up to have 10 experts help you work through your toughest and trickiest leadership problems TODAY

Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.