5 tips for entrepreneurs setting 2021 goals

In my experience, goal setting at an early stage startup can appear simple, but the real challenge lies in balancing discipline with agility.

5 tips for entrepreneurs setting 2021 goals

[Did a friend forward this your way? I write about trends in startup communities and social impact – with a few takes here and there. If you're into it, please subscribe here.]

Quite the year we've had. A global pandemic. A(nother) horrific instance of police brutality. A polarizing election. Murder hornets. There's no way around it, folks - 2020 has been a dumpster fire. Let's chalk 2020 up as an "L" and look forward to what we all hope is a brighter future.


With 2021 around the corner, people, companies and communities are setting goals. Startup leaders are responsible for a few things: don't run out of cash, articulate an inspiring vision with confidence, and create an environment where people can do their best work. Goals tie these together.

As a founder, I've conducted extensive research about goal setting frameworks and explored a few quarterly experiments, but ultimately learned the most about OKRs from trial and error in a couple years at the helm of a startup.

In my experience, goal setting at an early stage startup can appear simple, but the real challenge lies in balancing discipline with agility.

Here are a few thoughts that I hope might guide your approach to 2021 goals.

Tip #1: We're not out of the woods (at all)

In the last month, the medical community has announced several vaccines with the promise to eradicate the pandemic. Researchers have pioneered new techniques to validate solutions in record speed. Humanity let out a collective sigh of relief with the hope of a light at the end of the quaran-tunnel™.

Yet, major obstacles remain at home and abroad. The US continues to break daily records while healthcare workers and at-risk groups stand by to receive vaccinations. In New York City, daily cases near an all-time high as the first 170,000 vaccines arrive. The initial state-by-state distribution of vaccines could be as fragmented and unpredictable as social distancing and testing measures. Massive financial challenges will continue to hinder the economy and many individuals nationwide.

Abroad, the vast majority of countries (83%) have yet to purchase enough vaccines to cover even a tenth of their populations. The world will watch closely as the UK rolls out a nationwide vaccine distribution plan, India grapples with a recession and many newly elected world leaders set the tone. Political corruption and poor infrastructure will surely leave millions living in poverty without aid for months to come. Despite the daunting resurgence and obstacles ahead, progress now feels tangible.

Projections for vaccine distribution stretch well into 2021.

Ultimately, 2021 is going to be far from a normal year. The whirlwind of the last 9 months has put many startup leaders to the test, but the gauntlet is far from over. How does one set goals in this environment?

The best advice I heard was from entrepreneur David Aktary:

"Times of economic certainty don’t actually exist. Set your goals and strive to reach them as best you can, given the ever-changing circumstances."

Goal setting is an imperfect exercise, and this year is certainly no exception. Scale your goals to the realities of today's world. Consider your goals early and often, check them weekly, and adapt them monthly to tell the right story for your venture.

Tip #2: Find the right size

The most prolific writing on OKRs relates to big organizations. The company > team > individual model and all of its cascades can be overwhelming. For an organization under 50 employees, I've personally found that these layers can create undue operational burden. While employee development and feedback loops are essential, reviewing top-level goals together will create focus and alignment.

What about tools? At Union, structured Google Sheet for company-wide goals has proven to be enough for us. With each new quarter, we usually land on 3-5 company-wide objectives across business, product and internal verticals, each with a few metrics measured weekly or monthly.

A quick look at how Union tracks its OKRs in a Google Sheet.

There are volumes of great books, articles and tools. Find what works for you as a company, and especially as a leader.

Tip #3: Walk the talk

Even small startups can make a difference with measurable social impact goals.

In the tech world, necessity has finally held a spotlight to the many generational disparities in wealth, opportunity, and quality of life. Rampant abuse of the natural environment is actively creating regressive displacement and social strife. People, companies and nations are revisiting their priorities with pressure from public markets, conscious consumers and employees who care. Social impact investment performance is beginning to follow.

This year brought many important issues to the fore, leading many to reflect: How am I as an individual reversing centuries of inequity? How am I reducing my carbon footprint? How am I supporting the many jobless and underemployed? And what can my place of work do to amplify and expand upon these efforts?

Well, goals help get sh*t done. Make it actionable! If your organization wants to make diversity a priority, your OKRs should reflect that. If the company is growing, set ambitious, hard numbers for company diversity, particularly for leadership positions. If you aren't hiring, consider initiatives that create a more positive, inclusive culture – product accessibility audits, demographic tracking in UX research, or marketing efforts to amplify underrepresented voices.

Companies can also take easy steps to offset their emissions or even passively remove carbon already in the atmosphere. For a more active approach, go plant some trees as a team.

Many charities, food banks and mutual aid organizations exist to help those less fortunate. Companies can band together to broaden their impact with donation matching and volunteering initiatives.

If you want your company to back a worthy cause, put a number next to it.

Tip #4: Give your OKRs a home

For an early stage startup, talent can be the major differentiator. While the debate rages on around the importance of a startup idea, market and more, it takes smart and adaptive people to make it all happen. In 2021, this will be especially true – the right people in the right positions will drastically increase your chances of success.

Goals need owners to be effective. As you plan your objectives, the owner of each key result should understand that they are responsible for updating a metric, reporting on it to their manager, and leading every effort to deliver, unblock or adapt if things aren't on track.

Don't forget the essence of the game: it's about the goals.

Once your goals are set, stick with it! Personally, I became far more productive with an amazing Chief of Staff who held me accountable. Every week I share my top 3 priorities and am expected to provide updates on each 3 days a week.

In 2021, leaders should take extra measures to foster shared ownership and peer accountability – your teams will be more empowered, aligned and effective.

Tip #5: Make it interesting

Once set, goals should be discussed often and updated frequently. If leaders are talking about goals enough, they're probably tired of hearing themselves talk about goals.

But experience has taught me that a goal review screenshare at the All Hands can cause eyes to glaze over. Let's face it – while OKRs can be crucial to success, reporting on them can be mundane, repetitive or even demoralizing.

As with many aspects of a business, goal setting ties into team culture – an area where companies have been pressure-tested in 2020. As an essential company function, goal setting should be inclusive, transparent, and collaborative. For a primer on culture, look no further than the late Tony Hsieh.

"I believe that getting the culture right is the most important thing a company can do." - Tony Hsieh

When it comes to reviewing goals, I've found that these tactics can help make it interesting:

  • Cofounders and senior leaders can rotate sharing weekly updates.
  • Pre-recorded videos sent in advance can permit the team to absorb context at their own pace.
  • Many digital whiteboarding tools can make brainstorms far more collaborative. Try different formats until heads nod in excitement.

As we turn the page and enter 2021, remember that goals are a means to an end, and adaptability is your biggest asset. Good luck out there.

P.S. Taking care of a startup begins by taking care of yourself. This is a topic for another post, but I'd recommend setting aside time for personal reflection and found this template helpful.

[Any thought or comments? I want to hear from you! Please send any feedback my way.]