As the year wraps up, many SaaS leaders are already looking ahead — setting budgets, forecasting headcount, mapping product releases. But here’s a question we don’t ask enough:
Are you presenting yourself as the kind of leader you aspire to be?
That question isn’t just personal — it impacts how your teams operate, how your customers learn, and how your business grows.
A strategic year-end review isn’t about nostalgia. It’s about sharpening your edge.
As Lincoln put it, “Give me six hours to chop down a tree, and I will spend the first four sharpening the axe.” The same goes for leading a Customer Education team, launching an Academy, or scaling a program with more impact. Reflection is your blade.
We’ve compiled 13 powerful questions designed for SaaS execs and Customer Education leaders who want to reflect with intention — and plan with clarity.
From a game-changing product launch to a breakthrough customer success story — what wins are worth remembering?
This question builds gratitude and momentum. Leadership is demanding. You need fuel to keep going.
What did you learn about:
Don’t just capture lessons. Turn them into playbook-worthy insights.
Whether it was from peers, execs, or customers — unmet recognition creates invisible friction.
Give yourself the acknowledgment you didn’t get. Then use that awareness to lead others differently.
Look at your calendar, projects, meetings, even content types. What lit you up? What wore you out?
A clear-eyed audit here can inform how you spend your time and energy next year.
Before you set your vision for the year ahead, close the loop on the one behind you.
That might mean celebrating wins. Or confronting a tough moment you didn’t fully process. Make peace with it — so you can move forward without baggage.
Don’t censor yourself. Imagine you’re a year from now, and everything clicked.
What did success look like — for your Academy, your team, your role?
This is your blueprint. It starts with imagination.
Behind every business goal is a deeper motivation.
For example:
When you connect goals to outcomes that matter, they become meaningful — not just boxes to check.
Big goals fall apart without structure.
Break things down into what’s in your control:
The secret isn’t ambition — it’s consistency.
Close your eyes and imagine that everything went right.
How did you spend your days? What did your team accomplish? What did your customers say about their experience?
Now ask: What did I stop doing to get here?
The answer might surprise you — and clarify what needs to go.
Internal blockers? External dependencies? Budget? Bandwidth?
List them all — then name the actions you’ll take now to mitigate them.
Accountability doesn’t have to be rigid. It can be motivating.
Try:
Clarity creates ownership. Ownership creates results.
Spoiler: they will.
The best leaders plan for turbulence. Build in grace and recovery paths — for yourself and your team.
In SaaS, we sprint from one milestone to the next.
But if you don’t pause to celebrate — especially as an education leader building long-term impact — you burn out, and your team does too.
Celebrate the small wins. The course launches. The learner stories. The Slack praise.
Progress deserves recognition.
The questions we ask ourselves shape the leaders we become. Take time to reflect and reset. Because the strongest Customer Education programs aren’t just built on content and systems — they’re built on clarity of purpose and leadership alignment.
We help high-growth SaaS businesses start and scale Academy programs that drive adoption, retention, and customer success.
This article is part of our self-leadership series — because building great programs starts with building great leaders.
If you’re planning for a big year and want an advisor in your corner, let’s talk.