My post on saying “no” to grow generated some great conversation in the comments. It also got me thinking about the problem from the other side: How to find the right things to say “yes” to in your development plans.
I was out west this week for our E-commerce Summit and asked leaders from our portfolio how they manage strategic priorities. It was portfolio power in action and the thoughts below are the result.
Adjusting the focus from high-level corporate vision down to strategic initiative and on to project definition and then to tactical next action and back up as quickly as possible is something I wish I had been better at as an operator. Founders can get stuck firefighting and micro managing, for months on end because the company is an embodiment of something that has been in their heads for years. Speed and agility are critical to a start-up and the ability to switch altitudes fast can be the difference between failure and success.
We can force altitude switching with 6 questions and when done right, the quality of the decisions will skyrocket.
1. Why are we doing this?
Clarity of purpose and explicit alignment with the vision for the business are critical to these decisions. Try to imagine the initiative is a success in every way and then imagine what that means for the business as a whole. If you are happy with the impact, it is something to say “yes” to.
2. Why haven’t we done it before?
Once you decide to pursue something, asking why it hasn’t been done already is a great way to expose constraints and limitations. Breaking the initiative into components and evaluating the goals of each component will also help you see if the team is working on pieces of the problem already or, equally importantly, has decided not to pursue it. The need to re-prioritize existing efforts in order to push the new initiative forward is important to recognize and communicate.
3. How will we do it?
This is about creative thinking and generating as many ideas as you can. “Brainstorming” is a topic to itself, and everyone has different takes on the most effective ways to manage creative sessions. (IDEO has some great slides on this) In my experience the most important thing is to get away from “No, because…” The goal is to capture the details of what success will look like not evaluate barriers to achieving the success you envision. No judgment, most ideas wins.
4. What is the best way for us to get there?
Once you have a lot of good ideas, you need to organize them through a process that accounts for your current position, team strengths and areas of weakness. This is a curation process. No ego, best idea wins.
5. Have we left anything out?
Repeat the “create” and the “curate” process again (and maybe again).
6. What should we do first?
It is critical to prioritize the projects and next actions if you expect anything to get done. Decide what should be dropped if anything, and decide ownership and accountability for what remains – who is responsible for each project and next action, and who will play supporting roles (if any) on each.
Access to this advice would have helped me say “yes” to the best ideas and eliminate the rest more quickly in my former life. I hope you all find it helpful. Also, thanks to everyone in the portfolio who helped me with this and I look forward to suggestions for improvements and refinement of these six steps in the comments.
***A shout out to Eric Koger at ModCloth for pointing me to The Natural Planning Model as described by David Allen in Getting Things Done for additional reading. If you don’t want to read the whole book, there is a good summary on this MindZone wiki.***

#1 by James Reinhart on March 8, 2010 - 9:23 pm
Phin,
I like your thinking here. The only thing I'd add in my (limited) experience is trying to decide what matters in the context of your next milestone, not ALL milestones. Brainstorming sessions can yield tremendous creativity and unless everyone has a sense of what the brainstorming is about – i.e. “lets think about what it will take to acquire our next 10,000 customers” versus say “how do we make the site better?” – they can end up being paralyzing because there is so much to do. We've tried to have big sessions followed by a series of focused breakout sessions around the yesses. For example: customer acquisition brainstorm -> SEO as critical success factor -> brainstorm components of SEO -> identify owner of SEO -> working session on SEO -> implementation plan -> regroup and evaluate. Gotta fly high and low to move the ball forward on all the dimensions.
#2 by phineasb on March 8, 2010 - 9:36 pm
This is a great point.
Having a clear purpose and focusing on specific goals to frame the conversation is key. Every brainstorm can't be about “where are we going as a company.” I think the total company process is fractal in nature, in that if this is done right, the same process that works for the company as a whole can also work for decision making for the smaller pieces that make up the greater whole.