For CXOs For CEOs

Recapping Navigating Choppy Waters: A Year in Retrospect

Whether you’re the leader of your business, a board member, or an executive preparing to present your accomplishments to company leadership, the end of the year signals an opportunity to reflect and report on progress, learnings, and performance.

On December 6, Bolster hosted the fifth installment in the Navigating Choppy Waters series. Our panelists, Ari Paparo (CEO, Marketecture) and Ana Chaud (Startup Advisor, CEO, Lodestar) discussed how to reflect meaningfully on the past year and shared advice from their own experiences. Watch the recording.

Running A Retrospective

Start on the same page.

“Whenever I do strategic planning with my team,” Ari said, “I first show the slides from the previous planning session.” The review refreshes everyone’s memory and helps ensure the entire team begins the retro with similar context and topics in mind.

Of course, priorities or circumstances may have shifted, and it’s likely your team didn’t follow every aspect of the plan. This is where everyone brings their own perspectives, updates, and knowledge—but starting from a shared understanding is key. From there, you can discuss where you stuck to the plan, where you deviated from it, what you accomplished, and where you may have fallen short.

Conducting a review of your initial plans and actual business results is vital. As a result, you and your team will better understand where you stand as well as your capabilities, strengths, and areas of opportunity before you jump into planning for the next year.

Let’s step back for a moment, though. “The end-of-year metrics shouldn’t come as a surprise,” Ana said. Whether your team is exceeding their goals or moving slower than planned, you should know—at least generally—what’s coming in the review. Good leaders are paying attention throughout the year.

This looks different for everyone. Whether it’s through quarterly updates, continuous feedback, or another strategy, you and your team should maintain awareness of your progress against your goals.

When the time comes to conduct a retrospective, you’ll be able to dive deep. This is where your team has an opportunity to discuss what worked and what didn’t. If there are goals or milestones left incomplete, you can decide whether they’re still relevant and should be carried forward. Together, you can review your accomplishments, growth, and learnings from the year. That’s where the true value of the retrospective is.

Success Metrics and Growth

We asked the panelists which success metrics they emphasize. How do you determine how business is going?

“Internal situations don’t always match external circumstances,” Ana said. She’s a proponent of understanding the external circumstances and how they impact your business, but staying internally focused. There are areas where it’s appropriate to compare your organization to the rest of the world, but generally, she finds it more helpful to look inward. How did your team measure up to your goals? How have you grown as a business? How do your results compare to previous years?

As you review your internal success metrics and consider your path for growth, Ari mentioned, startups “probably need a VP of finance—or a fractional finance leader—earlier than you think you do” (Bolster can help!). Whether you hire someone full-time or fractionally, they’ll ensure you’re tracking and measuring the right financial metrics, and help you reach your goals. Having the right leaders on your team can make all the difference.

Having healthy leaders on your team also makes an impact. “The well-being of the leader determines the well-being of the organization,” Ana said. CEOs who are prepared for the scope of the job and who have support are less susceptible to burnout. This is true for all leaders, really. As you conduct a retrospective for your organization, encourage your leaders to check in with themselves and review the year on a personal level.

At the end of your retrospective, you should have a better understanding of the past year’s business performance. You’ll have reviewed goals, progress, and learnings, and be in a better position as a team to move into the new year with confidence.

Did you miss the event? That’s totally fine—the recording is available and only 30 minutes long! To find it—and sign up for our next event, a VC-led Equity Market Temperature Check—click here.

Keep up with the speakers:

Ana Chaud: LinkedIn, Twitter

Ari Paparo: LinkedIn, Twitter