How To Lose Customers & Alienate People
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How To Run An Offsite


If you’ve worked in a growing startup company for more than a few years you’ve likely noticed when the executive team schedules an offsite meeting and wondered what happens there. Sadly, there’s often a lot of bonding and not enough actual work. So let me suggest a framework for how to lead an effective offsite meeting.

First of all, you must be clear: what is the purpose of the meeting? If you think it’s for team building then I will forgive you if you’ve never seen a great offsite. Yes, team building can happen. But if that’s the main purpose, you are setting a low bar. In my experience the purpose of an executive offsite meeting should be one of three things:

1. To consider and plan for a change of strategy

2. To develop a set of priorities in advance of the annual planning cycle

3. To work on the company’s hardest unsolved problems in a creative forum

In some cases, perhaps it is a combination of these items. If you cannot determine a priori the purpose of the meeting, it will likely be a waste of time and money. You can do all the trust exercises you want, but if the executive team is not working on the business, it’s unlikely there will be any lasting impact. After you’ve left Austin, Napa or Tahoe you will still have the same problems you had before.

Developing The Next Generation of Leaders

Once you are clear on the purpose, it is much easier to then identify the key people and topics you want to cover. Maybe you’re wondering: if it’s the executive offsite isn’t it just for the executives? Yes, that is one approach. But I have found that if you expand the group slightly, to include the next-level up-and-coming leaders, you can have far more impact.

In fact, I would consider another purpose to the executive offsite can be:

4. Develop the next-level of managerial talent

Bringing in a broader range of participants can be especially helpful when tackling the myriad of “hard unsolved problems.” The goal is to fully integrate everyone into solving complex problems that often span beyond a single department. Everyone has a seat at the table. Every is expected to contribute. This is not a spectator sport.

You may want to brainstorm the topics in advance to ensure focus. Once the topics are determined, I have found it works well to assign each topic to a pair of people. Ideally, colleagues who might not otherwise be working together. Perhaps a VP paired with a Director in a different department. They should prepare enough material to kick-off a discussion with the entire group, then break down into smaller groups to come up with ideas.

Work on the Hard Problems

At MySQL, we often had a nagging problem of how to improve product differentiation. MySQL was an open source database and people loved it. But it was not always clear why and when someone should pay us. We talked about the problem all the time, but we weren’t making much progress. So I proposed that at our next executive offsite we do three things.

1. We make differentiation the major topic of discussion

2. We invite half a dozen up-and-coming leaders in the company to join us at the meeting

3. We pair up leaders to lead a workshop on the problem

I organized the session and reviewed the materials in advance. I was not asking the leaders to solve the problem (which was unlikely) but rather, to frame the topic and then lead a workshop whereby we split into groups to brainstorm ideas.

Bertrand and Edwin, two Director level managers led the effort. It was brilliant. They brought a fresh perspective to the problem. Bertrand provided an excellent example of a commoditized product that could be differentiated (bottled water!) that reframed the problem in a creative way. It caused everyone in the room to think differently. And it was inspired people to became unstuck from earlier views. That resulted in much more creative idea generation than we had seen previously.

While I won’t say that the problem was completely solved in the course of two days, it did pave the way for us to develop further enterprise differentiation. Instead of just asking ourselves “Why can’t we follow the Red Hat path?” or “Why don’t we close source some features?” we got much more creative, coming up with a subscription model that solved more problems of our Enterprise customers, delivered more value, and provided differentiation.  Ultimately, the subscription model became the growth vector for the company and led to a billion dollar sale to Oracle. 

One of the key things I’ve observed from offsite meetings is it’s important to get a cross-section of people across different disciplines and backgrounds to tackle hard problems. If you just ask the product team to solve all the product issues, they will eventually run out of ideas and get stuck. But sometimes, when you bring in someone from a different field, whether it’s Finance, HR or Sales into the brainstorming you will get unexpected questions, examples, and suggestions that might never have come up otherwise.

Follow-Up for Required

Offsite meetings can be a great a way to generate creative ideas and momentum. I remember one executive complained later that while we generated a lot of ideas, where was the follow up? Ultimately, it is up to the functional leaders, the head of Sales, the head of Marketing, the head of Engineering and so on, to determine (with input from the CEO, of course) which ideas and initiatives should move forward. In my experience this results in the best ideas getting the resources they need. To do otherwise is to circumvent the line authority of department leaders.

This is one reason that it can be helpful to hold an executive offsite meeting before you undertake the annual planning process. It drives creativity and focus before operating plans are finalized.


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