How to Approach Strategic Planning When the Sky is Falling

Can you remember when you used to gather in person with your team to define your roadmap and reassess your company’s collective priorities? Every quarter, our team at Pillar VC convenes for a strategic planning session to decide how we’ll invest our time and energy in the months ahead; last week, we held this meeting for the first time over Zoom. While we’ve only been working remotely for a few weeks, it feels like the world around us has changed at lightning speed. 

In the midst of so much uncertainty, a practice that has always served as a source of reflection and provocative discussion was suddenly accompanied by a critical need to address our “new normal”. What has changed in the macro environment? What’s most important to our team and our portfolio right now? Which priorities most deserve our focus and energy? How should we balance immediate needs with setting ourselves up for long-term success, particularly when the next 12 - 18 months are unclear? The importance of slowing down to speed up has never been so acute.

While we’re always cautious to focus on a few initiatives that we can tackle with success, we were particularly thoughtful about making room for the unknown this quarter. When you’re dealing with uncertainty, be sure to create space for fluid change––chances are you’ll need room to adapt. 

1. Keep What Worked Best Before 

When all systems run normally, we turn to an approach that worked well for us when I was on the management at Pluralsight. We’ve made a few small tweaks, but it works just as well for us as a 5-person team at Pillar. 

Rocks: The strategic playbook we use is centered around the concept of rocks and pebbles in a jar (watch this short video). If you put all the pebbles in first, you won’t have room for the rocks. If you put the rocks in first, the pebbles will fill in the gaps.

Rocks = big meaningful initiatives that move the needle

Pebbles = daily work

This framework is derived from the 7 Habits of Highly Effective People, and forces you to identify a small handful of meaningful initiatives that the team will rally around achieving each quarter. Another book that was influential in how we approached these meetings and our relationships with each other as an executive team was The Advantage, by Patrick Lencioni––also worth a read.

While much has changed in the last few months, your Mission, Vision & Values have likely remained consistent. These core tenants of your company are typically determined once and serve as the constant guiding forces of your organization. The boxes at the top of the page align with mission, vision and values. In theory, these should never or only rarely change. Every word matters. I’ve included ours for Pillar below.

The last box is usually the only one that will change quarterly — what is most important now. With so much unknown, what do you still know to be true? What will make or break your company this quarter? Perhaps it’s simply ensuring that you’ve put time and energy into developing a solid contingency plan.

Maybe now is a time to double-down on customer centricity and retention. Your business may also be confronted with a new opportunity in light of the pandemic; should you point your resources in the direction of a partnership or revenue channel that was never available to you before? When the sky is falling, what is the stake you want to put in the ground? 

This doesn’t necessarily mean that your core principles completely change or shift. Your underlying values as a company likely remain consistent, but now is a good time to take a temperature check. Ask yourself and the other leaders in your organization if the recent dramatic shift has also shifted who you are as a collective group of people pursuing a discrete set of business goals.

Chances are, what you and your colleagues determined were the most important areas for focus no longer feel as critical; much has changed. The annual themes are broad objectives for the year related to specific aspects of your business.

These themes guide your rocks each quarter; if you want to achieve them, you need to work on projects (rocks) that further their development. Examples might include broad themes like stand up marketing automation infrastructure, prove a repeatable sales model, or maintain a diverse and inclusive culture as we scale.

Revisit your annual themes to consider whether they remain true. Don’t be afraid to throw them out and start over. You couldn’t possibly have anticipated what the world would look like today when you kicked off the new year a few months ago.

Take the time to repeat the exercise of prioritizing the big buckets of work you should pursue this year. Once you have a revisited set of annual themes that feels relevant in the new normal, identify a small handful of goals or rocks that you will achieve as a team. These should be strategic initiatives that drive the business forward––the fewer the better. 

Here are a few aspects of strategic planning that shouldn’t change in uncertain times. Each rock should have an owner, who is responsible for reporting on progress at each weekly management meeting. Without ownership, that rock likely won’t budge.

Each rock should include an explicit criteria for success––i.e. how will we know if we achieved it?––ideally quantifiable. During each weekly meeting, we review the status of each rock, and evaluate whether we are making enough progress against the criteria for success. 

Furthermore, as part of our discussion, we evaluate whether pebbles are impeding our progress, or whether there are other hurdles we need to address or tradeoffs we need to make to succeed. The key to getting your rocks moving in the right direction is to make them few and meaningful (we will often challenge each other — is that a rock or a pebble?).

You can tally the progress with your very own Rocks Dashboard spreadsheet. We review this every week during our team meeting.

Just as important as what we are now focusing on is what we aren’t. Those sidelined rocks, the ones we discuss but don’t pursue, get thrown in the parking lot. 

Parking Lot: A list in a tab in our dashboard that we save and revisit next time. Likewise, throughout the quarter as other new ideas emerge, we stick them here for discussion next quarter.

We typically revisit our progress quarterly. We host a one-day planning session during the last week of the quarter, every quarter. We review the prior quarter’s rocks and discuss what we achieved, where we missed and why. This is in addition to reviewing the rocks on a weekly basis during management meetings.

In advance of our quarterly planning meetings, we ask people to make a list of potential rocks for the new quarter. Individual team members will often prepare short presentations or volunteer to guide a group discussion about specific potential rocks, as we shape our thinking. We then typically have a group discussion to land on final rocks by the end of the day.

Once you’ve aligned on your priorities for the quarter, share them broadly with your leadership and with every individual in the company, so you’re all aligned and rowing in the same direction.

Repeat yourself. Be transparent as information changes, and lean in to meeting more frequently as a team to revisit your priorities to be sure they still hold true. Quarterly might not be the right cadence anymore––figure out how frequently you and your team need to meet to stay on top of the changes in your business.

Whether you use this or another framework, purposeful planning is an important way to make sure your team is aligned and is rowing in the same direction. This is particularly important when times are trying and unpredictable. Done right, you’ll keep your organization on track in uncertain times and ensure that every member of your team can help drive the business forward.