The 5 Mistakes Startups Make When Setting and Achieving Objectives

Startups are not short on ambition. Founders dream big. Teams move fast. Investors push for scale. The problem isn’t usually what startups want to achieve but rather how they work to get there.

After working with dozens of early-stage companies, I’ve noticed a recurring pattern: startups consistently struggle to set and execute objectives in a way that drives meaningful, aligned, and consistent progress. Companies set wonderful goals in the beginning of each year, excited to get work on them. But 3-6 months in, it all falls apart. Like clockwork.

Here are the five most common (and costly) mistakes I see and how your team can avoid them.

5 Biggest Mistakes Startups make when setting and working to achieve objectives

1. Poor Alignment to Annual Goals

Setting annual goals feels great. They give the team a sense of purpose and ambition. But too often, those goals go stale by Q2. Why? Because teams set their quarterly objectives without reconnecting them directly back to those big-picture outcomes.

What you get instead is reactive planning. Teams chase shiny new opportunities, fixate on urgent issues, or build quarter-by-quarter without a strategic through-line. The result is busy work, not business progress.

What to do instead: Revisit your annual goals in your quarterly meetings and ensure the team is aligned on those goals. Use them as the foundation to define what really matters next. What do we need to do over the next 90 days to put us on track for our annual goals? Build out a roadmap for each goal in 90, 180, 270, and 360 days. Every quarterly objective should be a logical step forward on the path to your annual vision. If it’s not aligned, it’s noise.

2. Too Many Priorities

Startups love speed. But moving fast in ten directions isn’t the same as making progress. Many teams overload their quarterly plans with too many objectives. It’s understandable; there’s so much to do. But when everything is a priority, nothing gets the attention, energy, or depth required to succeed.

It’s not just about team capacity - it’s about focus. Diluted attention leads to diluted outcomes.

What to do instead: Pick 1-2 key objectives per annual goal. That’s it. Ask: “If we only accomplished these things, would it move us meaningfully closer to our goals?” If the answer is yes, you're focused. If the answer is no, you're just staying busy.

3. Objectives That Are Too Broad (or Too Big)

Here’s a classic example: a startup declares “Become a thought leader” as a Q1 objective. Ambitious? Yes. Achievable in 90 days? Absolutely not.

This happens all the time. Teams write objectives that are so broad, vague, or large in scope that they’re practically impossible to act on, let alone achieve. These often belong in an annual plan, or they need to be broken down into something more tangible and time-bound.

What to do instead: Make quarterly objectives focused and actionable. “Publish four high-value LinkedIn posts per week and land one industry podcast appearance” is specific, measurable, and realistic. You can still aim high, just break it into achievable steps that ladder up to the bigger vision.

4. Ignoring Progress Until It’s Too Late

Far too many teams treat quarterly objectives like set-it-and-forget-it agreements. They set goals at the start of the quarter, then go heads-down and only check in when the quarter is nearly over. By that point, it’s too late. If progress is off track, the window to fix it is already closed. Teams end up surprised by their own results, even though the signs were there all along.

What to do instead: Build a cadence of light, recurring check-ins (The Circle Forward method recommends weekly accountability and alignment meetings) to monitor progress. This isn’t about micromanagement; it’s about visibility, accountability, and continued alignment. Ask: Are we making progress? Are we stuck? Are our assumptions still valid? This discipline helps you course-correct before it's too late.

5. Treating Objectives Like Checklists, Not Learning Journeys

This one is subtle but incredibly important. Many teams treat objectives as binary: we said we’d do these things, we did them, so we succeeded. But that’s a dangerous oversimplification.

Just because you did the work doesn’t mean you got the outcome you were aiming for. If your strategy isn't driving results, the point isn’t to check the box. It’s to figure out why and learn from it.

Execution isn’t a fixed path. It’s an iterative, learning-driven process.

What to do instead: Build learning into your process. Treat objectives like hypotheses: “If we do X, we expect Y to happen.” Then observe, test, and adapt. This mindset creates resilience, drives smarter problem-solving, and gets your team closer to real outcomes, not just outputs. We incorporate a learning discussion into our weekly alignment and accountability meeting.

Final Thoughts

Great execution starts with great goal-setting. But it doesn’t end there.

The startups that consistently grow, iterate, and succeed aren’t just those with the most ambitious visions. They’re the ones with the most disciplined, focused, and adaptive systems for translating those visions into action.

If your team is struggling to hit objectives, take a step back and ask:

• Are our quarterly goals aligned with where we want to go this year (annual goals)?

• Are we focused on the few things that matter most?

• Are we identifying and solving problems as they arise, quickly and efficiently?

• Are we reviewing consistently, and learning our way into success as we go?

Getting these things right won’t just help you hit your next quarter. It’ll give you a system for hitting every quarter after that.

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