Two questions to guide any startup today, tomorrow and in the future

In a recent working session* with a seasoned founder, I think I found some gold in how they framed the conversation. The two questions that…

In a recent working session* with a seasoned founder, I think I found some gold in how they framed the conversation. The two questions that we worked to answer were

1. Where do we start?

2. Where do we go from there?

The CEO framed everything with the context of time and urgency — where we are today, what it means for tomorrow and how it impacts the long term future. For example, say you are thinking about how to go after a particular (large) market. The best target is often the intersection of who you could serve best given where you are today (“where do we start?”)and who puts you in the best position to move in the direction you want to go (“where do we go from there?”). This target changes as the company matures but I think these two questions are always relevant.

“Where do we start?” forces you to look at the 0–1 moment of any effort. It forces commitment to specific action and allocation of resources required to achieve your near term goal. This question also makes you address your priorities and acknowledge the tradeoffs you make when you choose a starting point.

“Where do we go from there?” shines a light on the “so what?” of the effort — it requires an articulation of the impact you expect your action to have and forces an honest assessment goals and desired outcomes vs. the cost required to get there. It provides the space needed to recognize that very quickly you will be moving FROM the starting point you chose TO another point you are also choosing. Every CEO I have worked with has a vision, but you have to connect that vision of where you want to go to your starting point and then define the direction you’ll take after you start. This link between effort today, the next step and the long term vision for the business necessitates alignment of near term efforts with long term strategy. Not connecting those is often what throws people off.

The conversation was very productive and I think a lot of that had to do with the framework of these two questions. It turns out the founder uses these two questions for macro strategic direction and the smallest tactical decisions. It works equally well in both situations and everywhere in between.

*A note for some context:

We don’t do typical investor updates where the founders spend a couple hours going through slides and then we, the investors, say, “Good work, keep it up” — instead, we do working sessions where the updates happen via email prior to the meeting (so we all have context) and where the founder defines success of the meeting with specific things they want to walk away having accomplished, agreed to or decided. We come to working sessions prepared with the combined knowledge and resources of our team and our network and then spend the time together diving deep into 2 or 3 key challenges or decisions that have to be made in the next few weeks.