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Five lessons we learned from making strategic shifts as a company
Strategic shifts are scary and exciting, and I'll share some tips and tricks if you're facing a lot of change and need to navigate it with your team
Over the past few weeks, we’ve made a pretty big strategic shift at work. (I won’t get into the details here though I’ll make a quick plug – if your sales team is looking for a tool to help automate demos and trials, check us out!)
From making the decision to sharing it with the team, I’ve learned a number of lessons that can be applied to other contexts as well – even if you’re not facing a major strategic shift for your company, you can use these lessons when navigating smaller decisions such as changes to a process or ways of working that will impact your team.
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First, treat the decision to be made the same way you’d think about pitching a net new idea/project/effort.
Concretely, what this means is that you should lay out your option set clearly. For each option, you should prepare a “mini pitch.” In our situation, we basically created a mini pitch document to outline our alternatives. In the document, we detailed the following:
Our perspective on the big picture – blue sky, limitless potential, long-term vision, etc.
The key questions to be answered through our hypothetical investment
Priority areas where we’d allocate resources and spend our time, which mapped to the key questions above
Metrics for success and tracking progress
Proposed staffing model and team breakdown
Basic budget and targets for revenue
Reasons we may not want to pursue this path (to play Devil’s Advocate with ourselves and prompt a healthy discussion for the alternatives)
This doesn’t have to be incredibly lengthy but going through the exercise of creating a basic answer for each of the bullets above can be quite powerful in revealing potential challenges, roadblocks, concerns, or other benefits.
After everyone on the exec team had a chance to read and digest the document, we set aside time to discuss and go through questions and concerns together. This made for a very productive conversation, where we focused on the decision rather than getting bogged down in random hypothetical scenarios or discussing hypothetical logistics.
Second, it’s okay (and important, probably) to mourn the old strategy and direction, but don’t let that postpone the timing of a critical decision.
This is a lesson that is much clearer in retrospect. Especially in a startup environment, it’s easy to be very emotionally invested in your work and a particular idea. For a few of us on the exec team, we realized that it was probably a complex mix of feelings that held us back from initiating the discussion about our strategy sooner. We probably should have had this discussion a few months ago.
My thoughts on how to avoid/manage this are:
Listen to external thought partners and also anyone on the team who has fresh eyes – they’re likeliest to see past things that others who’ve been around for longer might be more attached or biased towards
Practice healthy detachment from ideas or product areas – easier said than done, but remember, your worth is not simply your output/ideas/existing product. The company is more than just that, and when it’s time to move on, it’s time to move on
Give yourself designated space and time to mourn when you have to walk away from something. It feels silly to talk about mourning something inanimate, but when you do put a lot of heart and soul into something, it does take emotional energy to walk away. Remember what you learned from it, take those lessons, and go forth and conquer the next idea
Third, go all-in.
The alternative phrasing for this lesson is “Have a crisp and clear strategy.” This probably applies the most to anyone in a startup or small team environment. When we were deciding our path forward as a company, we considered a hybrid approach where we allocated some of our resources to our old strategy while focusing the majority of our team towards the new strategy. The more we talked about it, the more it introduced operational complexity, dilution of team focus, unnecessary admin overhead, and muddying of our marketing messaging. The flip side is that we felt it could have been a good hedge for us, but ultimately, with a small team and our goals for revenue and growth, it didn’t make sense to split the team up.
Going all-in also paved the road for an easier time bringing the team on the journey, which is my next lesson.
Fourth, bring your team on the journey with you after the decision has been made.
While the decision is being made, there’s a lot of whiplash back and forth. This can be distracting and confusing and worrying for the broader team. We shared the decision for the first time with the team a week after we’d discussed and finalized our plans as an exec team. Keeping it brief between our decision and the announcement was very important, as people tend to pick up on something serious being discussed and often can probably see signs that things are changing even before the decision is formalized/announced.
When we made our formal announcement to the team, we made sure to prepare lots of context. We typically don’t script our announcements but for this one, we wrote up bullets on what we would each present. Our agenda roughly covered:
A recap of our previous strategy and what had/hadn’t worked (including a summary of where we had invested)
A summary of the new strategic direction, i.e. the decision we’d made
The inputs we’d received from external advisors on this decision
What this shift would mean for the team in very concrete terms and benefits we expected to see for everyone
A recap of the process we took to get to this decision
What we were now most excited about, going forward
There were four of us involved in this decision, and we each covered part of the agenda. It was important for us to each speak to the parts that resonated the most with us.
After we shared all of this, we gave the team half an hour as a break and regrouped afterwards to answer questions. This was really productive, as it gave people some time to digest in the moment and come back with clarifying and follow-up questions. This brings me to my final lesson, which is:
Fifth, give people time to digest and process the changes. Follow up with them after a few weeks.
Over the past few weeks, since we made our announcement, we’ve had lots of 1:1s with different people on the team. Everyone has processed the change differently. We came into this knowing that there may be some people who aren’t as excited about the new direction as others. We knew that the right choice for the company in the longer-term was to go all-in and commit, and with that, we knew to plan for the scenario where a few people might decide that this isn’t for them. We were clear in our announcement when we shared all of this, and we addressed it directly with the team, encouraging everyone to take time to reflect and think further. We’ve been open to questions and discussion and kept a pulse on how people have felt in the weeks since the announcement.
Sometimes, major strategic shifts will result in some turnover. That’s okay, as at the end of the day, it’s really critical for everyone on the team to be aligned with the strategy and the direction that the company is going in. It can be tricky to navigate, but it’s also an exciting opportunity to turn a new page for a team or company and get a bit more laser focus on a specific direction or objective.
All in all, I’ve learned quite a bit over the past few weeks as we’ve made a strategic shift at work. Here are the five lessons learned:
Treat the decision to be made the same way you’d think about pitching a net new idea/project/effort.
It’s okay (and important, probably) to mourn the old strategy and direction, but don’t let that postpone the timing of a critical decision.
Bring your team on the journey with you after the decision has been made.
Give people time to digest and process the changes. Follow up with them after a few weeks.
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