Ask strategic questions

Not everybody is a brilliant strategist. And that’s ok. Yet every founder team need a strategy for how to develop and grow their startup, and what do you do, if the very thought of developing a strategy just gives you an uneasy feeling?

The simple answer is that you make it as easy as you can for yourself by ensuring that you have a simple platform from which you can get to work on your strategy.

There are many different platforms, you can use. With platforms, I essentially mean approaches. And there is one approach that is more powerful than most and which will easily help guide you through the process without too much pain:

Start by asking strategic questions.

What is a strategic question?

A strategic question is one that borrows from the “How Might We…”-methodology of the Google Design Sprint process (or maybe it was the other way around, doesn’t really matter) and allows you to frame your goal and aspirations for outcomes as a question.

A couple of examples:

How might we utilize our strength towards Segment A of customers to launch successfully with Segment B?

How might we grow retention in our customer base over 97% month over month?

Get it?

When you asks questions like that, you can start plotting suggested answers to them. You can word these like outcomes, i.e. “Launch 1:1 Customer Success offering for Premium Customers” and then look at which actions you will need to take in order to deliver on that.

When you have that sort of Christmas tree of objectives and actions – essentially an OKR structure – you’re well on your way to formulating a strategy: You will be crystal clear about what you will be doing, what the result is going to be and why you will be doing it.

The rest is – more or less – just a matter of getting it written up in a format that can be shared and discussed with your team and various stakeholders, before it becomes the new strategy to guide your venture towards even more more success.

But remember: It ALWAYS starts with being able to ask the right open-ended questions.

(Photo by Hello I’m Nik on Unsplash)

Reframing “How Might We…”

In my previous agency job I spent quite a lot of time working with the Google Design Sprint methodology, and I even got to a couple of moments of fame, when I both ended up teaching the methodology at the Danish Technological Institut as well as running a sprint for Google themselves.

There were – and are – a lot of great things in the Design Sprint methodology, which when applied in the right way can really bring ideas, conversations and work in general forward.

One of them is the “How Might We…”-question. It is a very elegant way of reframing a problem into an open-ended solution mindset, you can actually use as the foundation for working on fixing that problem.

There is one issue with the question though IMHO: It is not really good at framing the context of the question being asked.

But maybe there is a simple fix for that which makes the question even more powerful to ask? And not only for Design Sprints but for general conversations about vision, strategy and “What’s next?” for our company?

What if you started your “How Might We…”-question with a statement of fact to set the context?

Like: “Since we now have a sales model that works for other peoples products, how might we best introduce our own private label offerings?”

Or: “With maturity reached in our beachhead market, how might we go after the next vertical to grow our business?”

By doing it this way, you not only provide context to the open-ended solution oriented question. You also create a strong sense of why it’s important – almost “do or die” – for you and your team to spend precious time on looking to solve the problem.

And it will eliminate time wasting from those that will always be asking “Why?” whenever you try to introduce a new important project and leaving them with no or at least very little opt-out from stepping forward to help in coming up with the future solutions.

Essentially it underscores the “We” part of this collaborative proces. Which I think is key to the exercise and – done this way – a significant booster to get you set for a concerted, co-operative effort.

(Photo by Camylla Battani on Unsplash)