“It’s lonely at the top” is a cliche we’ve all heard. There is a reason things like this become a cliche—because they are almost always universally true. Leadership is lonely but why is that, and what can we do about it? 

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At Sidebar, we’ve spent an incredible amount of time thinking about this. Generally, what we’ve found is that as you progress in your career, a lot of things increase dramatically. The scope of your responsibilities gets broader, the complexity and importance of the problems and issues you face both increase, and the overall stakes of your decisions get higher. People talk about these changes a lot. What they don’t talk about as much is the thing that also decreases dramatically the more you progress in your career—the number of people you can turn to for help. We don’t think this has to be the case.   

It’s like our careers go through a funnel. When you started your career, your role and responsibilities were likely well defined, and the problems you faced were easy and relatively lower stakes. At the same time, you had lots of people to turn to for answers or help. You probably had peers and a manager and maybe even multiple levels of people above you you could turn to for answers. Often, you didn’t even have to seek an answer. There was someone there who just told you what to do in a given situation.  As you demonstrated your potential and moved up, there were fewer and fewer people to turn to…until, one day, there wasn’t anyone else to turn to. Instead, everyone is turning to you. This is one way to define leadership. If there is an issue or problem and everyone looks to you, you’re their leader, even if you aren’t their 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.

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There are lots of issues you may face as a leader, so what makes one a tricky problem? The situation needs to be RICH: 

• Responsible: 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. 
• Important: 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.
• Complex: 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.  
• Hard: You can’t solve this quickly because there are no easy or obvious answers—every potential path has tradeoffs.

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Sidebar was designed to help leaders work through these tricky problems, and 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. And, in parallel, the curriculum of the program helps to build additional skills and knowledge to help you face more of the issues of your career. 

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How We Solve Tricky Problems in Sessions

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At Sidebar we have a carefully crafted approach to problem solving that includes isolating not only the challenge but also the type of feedback that would be most helpful. This is followed by a reframing process that enables new perspectives. Once the problem is thoroughly defined, facilitated coaching enables collaborative exploration of the problem followed by an advisory session where ideas, suggestions and resources are shared. This process is always followed by definition of action items and, most importantly, accountability.

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This process has helped leaders with countless tricky problems. Here are just a few recent examples:

• A product leader at a large consumer Internet company was asked to do a keynote at a Women in Tech conference. She had never presented to such a large group before but her Sidebar group workshopped the speech and presentation, offering substantive content suggestions, speaking tips and encouragement that all helped elevate her performance tremendously. 
• A senior leader at a large academic health institution wanted to branch out and leverage her skills in the health technology industry. Her group joined calls to role play interviews, provide input on job description,  and help review proposed compensation packages. The group also suggested she explore non-traditional approaches and now she is consulting with a tech company as a side hustle, gaining the experience she wants without forgoing the stability she needs and providing a valuable bridge for both her current and new employers in a previously unimagined role.
• A product leader in transition was looking for a new role at other similar companies without much traction. His group encouraged him to start his own consulting company. Now, he has a podcast and clients.
• The founder of a fintech startup based on the East Coast was worried about lack of alignment with investors based in California. His Sidebar group helped him to plan a trip to the west coast, develop his presentation to his investors, and role played the conversation. The result was a clear path for coordination. 

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In fact, 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 Board 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.

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If you’d like to learn more about how Sidebar can help you with the tricky leadership problems you face, please check out the new section of our website.