I just finished a 8 hour board retreat for Gumball Capital, the nonprofit I cofounded at Stanford [1]. Our goal was to discuss information that board members had researched prior to the meeting, perform a SWOT analysis and get everyone on the same page as to where we stood as an organization, brainstorm ways to power continued growth and end with action items assigned to specific people.

Incredibly, we were able accomplish ALL of our ambitious agenda.

We got a lot done at the meeting and now have a lot of momentum going forward – plus we had some fun too. Having gone through a few looong/not-so-awesome board retreats for various organizations, I wanted to share some of what I thought caused this retreat to go so well. I’d love to hear people’s thoughts on these in the comments.
gumball board retreat

Note: Our retreat was masterfully facilitated by Tara Schubert and Duane Berger who coauthored The Facilitator’s Guide to Participatory Decision-Making and works at Community at Work. Definitely check them out if you’re doing something in the Bay Area.


  • Have clear goals set together ahead of time
    We made sure that before we started planning the retreat, the board and executive team were in agreement about WHAT we were going to do at the retreat and WHY. Related point to this is:
  • Know the difference between a outcome goal and a meeting goal. An outcome goal is what you want people to get out of a certain part of the meeting. For example, we wanted to get a better sense of what was going on in the microfinance industry and youth engagement with social causes. Our meeting goal was to 1) have people read a report 2) Have one board member highlight report findings and 3) Discuss for 25 minutes the findings
  • Build a great agenda; plan for both time & energy management
    You’ve got to spend some quality time in planning – at least one planning manhour for every seven meeting manhours [2]. Also, two things you learn is – 1) everything takes longer than you think so build in a lot of slack time and 2) people’s energy levels can be up (at the beginning, after a break) and down (right after lunch) so consider how tired people will be at various stages of the day and plan accordingly.
  • Make sure any pre-work is done beforehand
    In our case, each board member was assigned to present the group with specific findings. We did a good job of doing comprehensive research on topic (the state of microfinance & poverty alleviation, ways through which other student-run nonprofits have scaled, etc), synthesized it, and prepared it for the group. And everyone actually read the reports before the meeting.
  • A really good location & space
    These meetings are  typically all day so make sure you find an open space with couches (and preferably natural light). Often the location is removed from where the group typically meets – to better foster innovative thinking. Also you’ll probably want wall space for white boarding, charts or powerpoint (hopefully not!)
  • Complex meetings should be facilitated
    Every meeting needs to have some kind of facilitator to guide the discussion and keep people on track and on time – often this role is fulfilled by the person who called the meeting,or the team manager. In a board retreat, you’ll want to find yourself a talented external facilitator. We were lucky to get Duane.


  • Capture & display everything
    In addition to a facilitator, in a retreat such as this – you want to find a way to capture people’s ideas in a visible manner so they don’t go away. Often this is done a member of the team (switching off so no one is stuck with it) on either a whiteboard or a paper chart. We had another person dedicated to this role and she used paper charts, sticking them on various places around the room. I highly recommend employing both if you can.
  • Lots of snacks, drinks and breaks
    Willpower is a muscle [3] so when you have a bunch of people working through a difficult issue in a retreat, they can get depleted. Fill ’em up with cookies, chips, soda and other snacks. Plus breaks for bathroom, email and mental breathers. Continue reading

I’ve been mulling two semi-related work habits/beliefs that I think really contribute to individual & team success. I see them in a lot of people I admire and to be honest, they are habits that I’m glad I’ve naturally adopted.

1) There is Always More You Can Do

A few months ago, my coworker/direct report said to me “Well, I finished my all my stuff for today so I’m taking off early.” She does a great job, but her attitude didn’t rub me the right way. The next day I told her:

“If you feel pretty ahead on your work and you’ve been putting in long hours, sure, an early day is fine. But don’t make the mistake of thinking you’re actually DONE with all your work.”

You are NEVER done.

There is always more you can do – more industry research to do, more analysis to perform on the metrics you track, more phone calls could be made to a potential clients / partners, more practice on the presentation you have next week, more emails to write (perhaps to a coworker saying “thanks for your help on project X”), hell, more icon cleaning on your desktop to perform.

People who are sucessful get ahead because they recognize that the number value-adding activities are endless and are always doing much more than is strictly required, because you don’t achieve great thing by doing just enough.

2) Take Initiative / Responsibility for Improving Everything

If you don’t like some aspect of your firm or your work life – salespeople aren’t closing, the payroll process sucks, your boss never responds your emails, the press releases the PR team sends out are super-bland – don’t just blame someone or throw your hands up in frustration.

Do something about it.

Build relationships with the various departments and stakeholders so they trust & respect you. Learn about what they do and study industry best practices. Ask the HR team if they’d like feedback from the staff, have a meaningful conversation with your boss, forward your PR team a press release you like, talk to customers about what closed the deal for them and send the insights to the sales team. I hate it when people say “that’s not my responsibility” because it is a sign of apathy and helplessness that is not productive.

I’m not advocating shirking your own job responsibilities, just that you ought to  proactively address other areas if you feel you can help the firm improve its performance.

These ideas may be a little off putting to some people and it’s possible that they can backfire (burn out & angry coworkers come to mind) but I do believe that people who adopt these mindsets will ultimately add more value to their organizations and be more successful.

I just watched Up in the Air – it’s a movie starring George Clooney as a “career transition counselor” hired by downsizing companies to tell their employees that they are fired. He does it in a firm, thoughtful, and sensitive way, and he is very good at his job.

Up in the air movie poster

The movie is really good and touches on a number of interesting themes: intimate relationships, jobs & personal identity, re-evaluating life choices. However, the thing that struck me the most was the whole concept of a “firin

g consultant”.

Career Transition Counseling is a real thing (note the terrible 1990’s website) and apparently many companies exist to help other companies downsize. The practice is almost inevitable in our capitalist society as whenever there is a need that can be profitably served, there will emerge people willing to do it.

However, I believe that CTC is a cop out. Managers should personally hire and fire. That is their job. When you become the manager of other people, you are accepting a load of responsibilities and obligations to your company and your employees that you did not when you were “just” an individual contributor. I think all managers need to read, understand and agree to at least a basic list of statements like this:

As a manager I …

  1. Will only make decisions that I think will make the company more valuable.
  2. Will only hire people that I think will make significant positive contributions to the company
  3. Will always give clear and useful feedback whenever possible to help improve my employees performance.
  4. Will always seek to provide flexibility, organizational resources & fair compensation for my employees to do their best.
  5. Will tell employees to their face when I need to let them go, for whatever reason.

As a manager, you are responsible for your team and responsible to your company and its shareholders. People from the top and the bottom are counting on you and you have to deliver. If your division screws up, everyone pays for it, including you and your team, but also others and their teams. If you do well, everyone looks good – you, your team and your peers.

I’ve hired many people. It’s a fun job. I’ve let go of people, and it is definitely not a fun job. But you’ve got to do it. Own up to your duties, don’t pass them to others.

Potential managers must understand, passionately believe and agree to those obligations. If you don’t like giving negative feedback or firing people, and are unwilling to tough it out and do it yourself, don’t become a manager. We all know the world could use much fewer spineless bosses wandering around corporate America.

I haven’t had decades of experience as a manager of people, but I have led two volunteer-based organizations and of course I have worked with people who are my bosses. I’ve also read a lot about management and leadership. Here’s what I think creates effective organizations.

What’s your vision?
Without a compelling vision for an organization, it’s very difficult to engage your great people. If you aren’t excited by your vision, then it’s unlikely that anyone in your organization is. Your vision is what ties everything your organization does together. Every task should make sense in terms of the larger picture. Your people need to feel part of something greater than themselves. Speaking of people…

Your people are everything.
Find people who are smart, driven, not assholes and take initiative. Find out what they are good at, give them challenges to overcome, and make sure they have everything they need to overcome them. They say the secret to happiness is finding your strengths and using them. Incidentally it’s also what the best managers help their employees do. Organizations with great people do great things, as long as they avoid …

Bureaucracy = Death.
Rules are very useful – they keep people from doing stupid, wasteful and ineffective things. But nothing frustrates great people more than endless meetings, unnecessary rules and craploads of micromanaging. It also slows down your organization’s ability to adapt to new developments. Meaning you need to …

Embrace change, risk and failure.
The world is constantly changing and “we’ve always done it this way” is NEVER a good enough reason on its own for doing anything. The world is constantly changing, and if your organization isn’t, then something is wrong. You have to take risks, and some of those risks will result in failures. Know that. But do it anyway. It’s the only way to be great. But the flipside of that is that you need to …

Observe, model after and learn from the Best.
Only stupid people try to build everything up from scratch. Even if you’re doing something pretty radical/innovative, chance are, you can benefit from the best practices of other fields. Talk to people who have done what you want to do, study successful organizations. Use that knowledge to better understand what you and your organization need to do to achieve similar results in a new and different time/environment/situation.