The Strategic Planning Process We Used to Align Our 300 Person Team

“Running our strategic planning virtually and extending its participation in the process to 30+ people is bold . . . this is either going to be a 30-person-zoom-mess, or it could literally be a breakthrough in corporate strategic planning and alignment. Let’s go for it.”

That is a near-verbatim quote from Alex Estevez, a member of our Board of Advisors and strategic planning facilitator in the run up to our strategic planning ‘offsite’. It was clear that we could not meet in person safely. And the lesson learned from the prior year was that we need more participation, more co-authorship in the planning among our senior leadership team (this needs to be ‘our’ plan, not ‘my plan’).

That was almost five months ago.  

Fast forward to today, we just wrapped up our annual kickoff last week and I feel the best I’ve ever felt about our alignment to our vision and strategy as a company - partly because of this breadth of participation and co-authorship that we successfully pulled off (31 people participated in strategic planning!), and partly because I have had employees tell me so (“It’s never been more clear to me the long term path we are on; I understand how this year’s results and outcomes put us on that path; and I understand how my work contributes.”).

If we’ve had relative success in this area - of aligning 300-and-counting people - it’s because we have worked very hard at it. For years. Our planning process (which, in the end, is all about alignment) started roughly five months ago, and has been a dominant workstream for me and our entire Executive Leadership team over that time period. Months and hundreds if not a thousand hours have been invested collectively. It’s an enormous investment in time. And over 30 participants in the strategic planning process. In the early years of this alignment journey, the planning could feel frustrating and unnecessarily time consuming - the slog through misalignment, the planning and alignment “journey” that leaders all need to go on in order to have effective co-authorship in planning. That feeling is then amplified by broadening the audience of participants. To 31!

But over the years, we’ve realized that that investment of time, that messiness in the run up to alignment, that frustration - that’s just misalignment hiding in the shadows. It’s there and has always been there. Not going through this process just ignores it. This process drags that misalignment into the sunlight. The first few times it feels messy, it feels slow, it can be frustrating. Each time though, it gets better and better.

On the other side of it now, I know without a shadow of doubt that this is how we’ll continue to do planning. This is the way.

Let me go back to how we got here. Then I’ll talk about how we pull this off successfully this year.  

Our ‘Operating Rhythm’ Journey

As BetterCloud has grown as a company, as we’ve brought in more seasoned executives, and candidly as I’ve matured as a leader, we’ve put much more emphasis on our operating rhythm. The term ‘operating rhythm’ really didn’t mean anything to me 3 or 4 years ago but it’s “the breathing apparatus for the business”. It’s how you set goals, how you communicate, how you measure outcomes. And in the end, all those things are about ‘alignment’. It’s that repeatable drumbeat that makes sure everyone at the company is aligned, moving at the same pace, in the same direction. When ‘operating rhythm’ is done exceptionally well, it’s like clockwork, everyone knows it’s happening, they can feel it, they can rely on it, and they can plan around and within it.

Even when we were 100 to 150 people all of these things mostly happened naturally - it was easy to cascade information and get aligned. But as we’ve grown, maturing our operating rhythm is the only way we can begin to scale.

This ‘operating rhythm’ starts with our annual planning process. 

Because of COVID-19 and in pursuit of ever-tighter alignment, we tried something very different this year. And we did believe that this would either be a mess or a breakthrough in strategic planning and alignment. It was clear that it was worth the gamble. We were determined to ensure its success.

Our Strategic Planning Process

Here is how we approached our Annual Planning Process.

• Participants - We included our entire leadership team. For us that is all C level execs and their direct reports (mostly VPs), and is about 30 people (10% of the company). Let me emphasize that - we included 10% of the company in the strategic planning process. Not sure about those reading this, but that is a large portion of the company. Two planning cycles earlier we included 3% of the company. And in the years before that it was essentially me and our CFO. 
• Location - The planning was done 100% remote over Zoom. Of course we didn’t really have a choice in this. The truth is that we wouldn’t have been able to include this many people in planning if it was done in person… we probably wouldn’t have even tried. Traditionally, like most companies, we’d go offsite for planning, away from corporate and personal distraction for a few days. So much is missed by not being in person when it comes to building camaraderie but when it comes to the actual planning process we were able to get it all done remotely. You can read someone’s body language when they are uncomfortable with something, or disagree. Very hard to do on a two-dimensional screen and when there are 31 “boxes” of faces on the screen. 
• Timing - We dedicated 5 days straight from 11am-4pm ET to annual planning. We wanted to ensure that we didn’t overwhelm people with 8 hours straight of Zoom and wanted to ensure the start time worked for the people on our team that are on the West Coast. It was done 2.5 months before the end of the year. We’ve been working on doing planning earlier and earlier each year. A quarter out feels like the right window for a company at our stage. 
• Prep work - This is the hardest part of this entire process. You need someone to own this. The most important part of this is getting everyone who is ‘in the room’ to align on the facts. What does aligning on the facts mean? You can’t have people debating things like “what customer segments are we most successful in and why?”, “should we go international?”, “should we change our ICP (ideal customer profile)?” in the room. That type of stuff needs to be agreed upon walking in the room. If not, the offsite is consumed with reaching agreement on the interpretation of the facts, not on making strategic decisions. This was all consuming for our VP FP&A who also owns our OKR process for a couple of months. 
• Rules of engagement - We shared the rules of engagement ahead of time. People needed to have their cameras on the whole time, to ask a question or make a comment they would type ‘question’ or ‘comment’ into the Zoom chat. If they had questions they wanted to ask that weren’t as time sensitive we asked them to put it in a slack channel and the questions there were being answered asynchronously. Everyone had to participate and to ensure full attention folks were called on at random throughout the 5 days. 
• Technology/tools - This was done using Zoom for video, Slack for longer form questions (to keep the history of that), Miro for whiteboard, Google Slides for presentations, and Ally for OKRs. 
• Agenda
• Day 1: Foundation Topics - This is the only heavy presentation day. The most senior leaders present to the group things like: Our financial guardrails for the following year, and setting the foundation on things like what the next set of problems we want to solve, competition, market size, etc.
• Day 2: Setting our 3 year company level OKRs. We do this purely to help us reach and set audacious goals. It’s hard to think big 12 months out, but with 3 years, anything is possible. So we will spend 1 day agreeing on a set of 12 to 15 3-year OKRs.
• Day 3: Setting our 1 year company level OKRs. Now that we’ve got alignment on what success looks like in 3-years, it becomes very clear what has to happen next year to be on track to achieve the 3-year result or outcome. 
• Day 4: Departmental alignment. We break out functionally and each department makes their commitments for the year. Some departments are affirming and start planning based on company level OKRs that are cascaded to them, other groups make their commitments based on what the company has signed up for. The best part of the exercise is when everyone presents back to the group. Tension is good here, we encourage folks challenging each other to ensure dependencies are surfaced.
• Output - At the end of the session, everyone signs (manually the old fashioned way, there’s something about writing your signature out) an infographic with all our pictures on it, and our 1-year commitments.

• Company Communication - Following the offsite we did an 8 part all hands series with the company that includes deep dives on all the important ‘facts’, and culminates in all of our Annual OKRs. Just like with all the participants, everyone needed to go along a journey to understand the ‘why’ on certain strategic decisions. It’s much faster to just tell everyone the answer, but doing so skips over arguably the most important part for alignment and buy in - the ‘why’. We then reinforce the annual OKRs several more times as each department does their deep bottoms up planning in pursuit of the company level goals.

We have seen enormous benefits from this already - the entire company is aligned in terms of what our priorities are, people can work autonomously against the goals, and ultimately everyone feels ownership over the outcomes. I truly mean this, I think this type of planning process will have accretive benefits to our performance just because of how aligned everyone is.

I want to thank one of our advisors Alex Estevez who has been instrumental in helping us move in this direction, our CFO, Bart Hacking, our VP FP&A, Joe Iantosca, and my Executive Assistant, Dani Hunt. This wouldn’t have been possible without them.