Startup leaders don’t have the luxury of being either strategic or tactical. They must lead with strategic tendencies and be able to switch on a dime, roll up their sleeves and dig into the tactical as needed. This enables leading by example and supports the leader by giving them ongoing opportunities to earn their team’s respect and strengthen relationships/build trust. It also builds the foundation for a collaborative and cooperative culture, starting at the top.

TRUTH: Pivoting means you’ve failed. It’s not ideal. In an ideal world you start a company with:

• A significant market opportunity poised for accelerated growth.
• A team of exceptional caliber with the ability to effectively plan and execute.
• An innovative technology or business methodology that surpasses rival offerings.
• A compelling value proposition and strategic plan that clearly articulates how value is achieved, designed to secure necessary capital.

Another TRUTH: Sometimes you do start with these things, or you’re pretty close to having them all, but either you move too slowly or make too many mistakes before the market, the competition, and the world around you changes.

That means you have to pivot, adopt a fail fast approach with limited resources, or give up, which is the only definite failure.

At this phase, you might just end up in what feels like a pivot hamster wheel, which is why it’s so important to be strategic. Being strategic is the only way you can spot the opportunity that’s going to get you off that wheel and achieve product-market fit. You have to know how to identify it and have the courage to jump off the wheel and go after it when you find it. As a leader, you have to learn to trust your gut.

In a seed stage startup that has yet to achieve product-market fit, it’s common to have to make multiple pivots and do what seems like changing focus “all the time.” At least that’s how tactical people tend to feel if the strategy and the need for change of focus isn’t clearly defined and laid out for them.

As a leader, trusting your gut must turn into communicating that into a vision, a strategic plan, sharing it and motivating people to “come with you.”

The hard part here is letting go of baggage. It’s incredibly difficult if you lack comfort with ambiguity. Sometimes when you go through a few pivots, your experiences chip away at your confidence over time and trusting your gut becomes more and more challenging, even when you know you should.

Changing focus is not about adding new things while continuing to focus on old things that are no longer necessary to achieve your goals. There needs to be confidence and conviction in a new direction, and truly focusing requires letting go of what’s not working, even when what is in front of you seems ambiguous and scary at times.

Finding product-market fit is one of the hardest things a founder will ever have the privilege of attempting. Most founders fail at it. That’s why Unicorns are called… Unicorns.

As defined on Wikipedia, “Product-market fit, also known as product/market fit, is the degree to which a product satisfies a strong market demand. Product-market fit has been defined by its inventor as ‘a unique product offering that people desperately want.’” 

That’s why truly learning and adopting a fail fast approach is important if you find yourself in pivot mode. The thing about failing fast that is hard to do, is having the guts to walk away from what’s not working and focus on where your market is taking you. Failing fast only works if you learn quickly and adapt quickly.

Sometimes it’s helpful to imagine yourself floating on a raft in a body of water, no oars, you don’t get to jump in the water and swim to push the raft against the tide. It’s about learning to let the tide carry you when you don’t have the answers. The tide can be many things, but in this case it’s the market and your (potential) customers.

Note: This exercise was shared with me by a mentor a few years ago when I asked for advice as I was struggling to find direction in a critical moment. She’s too successful and private to name here… but I must give credit where it’s due.

I recommend you try it too…. Close your eyes for a couple of minutes and take some deep breaths. Sometimes you can see where the tide is taking you, or it might just feel good to float on that raft for a moment… that’s a great start.

But now, ask yourself some questions:

• Do any of my customers desperately want my product?

• If not, or you aren’t 100% sure: Which customers are closest to desperately wanting my product?

Now ask yourself this:

• Why would I focus on anything or anyone else?

Maintaining what’s working with regards to cashflow is an understandable necessity, so EVERYTHING you do from this point forward (if you are here) is:

• FOCUSED first on Product Market Fit.
• While juggling maintaining survival.

Anything you are working on must be prioritized as such. Meaning every team member’s energy is FOCUSED here first and everything that needs to be over-explained as to why it might fit in these categories, is where your real risk exists (aka derailment + wasted resources).

Again, it all comes back to strategic leadership, leading by example and constant, clear communication.

Shifting focus from old problems to new strategic goals is a common challenge in startups (and organizations of all sizes.) Here’s how you can guide your team to embrace and adhere to new goals:

1. Clear Communication of the New Direction: Clearly and consistently communicate the new strategic direction. Explain the rationale behind the shift and the expected outcomes. People need to understand the ‘why’ behind the change to fully commit to it.
2. Alignment of Goals: Align individual and team goals with the new strategic direction. Ensure that everyone’s objectives reflect the change and that there is an understanding of how their role contributes to the new strategy.
3. Leadership by Example: Leaders should model the behavior and focus expected of their teams. By visibly prioritizing the new strategic goals, leaders can reinforce their importance.
4. Regular Progress Updates: Track and share progress toward the new goals. Celebrate milestones to keep the team motivated and focused.
5. Address Cultural Barriers: Identify and address any aspects of the organizational culture that may be holding people back from embracing the new direction. This might involve changing policies, processes, or behaviors that are rooted in the old way of doing things.
6. Encourage Open Dialogue: Create an environment where team members can discuss challenges and hesitations about the new direction openly. Use this feedback to adjust plans and provide additional support where needed.
7. Problem-Solving Skills: Equip your team with problem-solving skills to address new challenges proactively. This encourages them to let go of old problems by focusing their energy on current strategic issues.
8. Strategic Withdrawal: For projects or initiatives that are part of the old problems, implement a structured phase-out plan. Make it clear when and how these initiatives will be concluded or handed off.
9. Mentoring and Coaching: Provide mentoring and coaching to guide individuals through the transition. This personalized support can help them to adjust their mindset and approach to align with the new goals.
10. Feedback Mechanisms: Implement feedback mechanisms that allow team members to report on difficulties they may be facing in shifting their focus. Use this information to make adjustments and provide support.
11. Change Agents: Identify and empower change agents within the team who can champion the new strategic direction and help their peers to adjust.
12. Review and Adaptation: Regularly review how the new strategy is being implemented and be willing to adapt plans based on what is or isn’t working.
13. Rewards and Incentives: Modify reward systems to recognize and incentivize progress toward the new goals. This could include recognition programs, bonuses, promotions, or other benefits tied to the new strategy.
14. Training and Resources: Provide necessary training and resources to enable team members to acquire the skills and knowledge required to address the new goals.

It’s also important to understand these concepts in relation to your team members and their development. At this stage of a business, the majority of them should be capable of wearing strategic and tactical hats as necessary, some more than others. If you’re a Founder or a CXO, your job is to help your people grow… (I know you know this, but do you truly practice it every day? That would be pretty hard to do in a startup environment… so always aim for more of this.)

The following framework examines the tendencies of Strategic and Tactical people and offers advice on how to Become more Strategic.

Tendencies of Strategic People

• Future focused
• Know the questions, not necessarily the answers
• Theoretical
• Curious, imaginative
• Risk takers
• Comfortable speculating
• Value planning
• Comfortable with debate, patient to let process evolve
• Love ambiguity
• Encourage diverse thinking

Tendencies of Tactical People

• Here and now, day-to-day
• Problem-solve, have or know answers
• Practical
• Linear, process-focused
• Risk-averse
• Concrete
• Planning is waste of time
• Need to have answers and closure

Becoming More Strategic

1. Cultivate a Visionary Mindset: Regularly set aside time for strategic thinking, envisioning the future of your organization or personal goals. Use tools such as vision boards or mind maps to visualize long-term objectives and the paths to achieve them.
2. Develop Strategic Questions: Instead of seeking immediate answers, focus on formulating strategic questions that challenge the status quo and stimulate forward-thinking. These questions should explore potential disruptions, innovations, and growth opportunities.
3. Foster Intellectual Curiosity: Dedicate time to read, research, and explore diverse subjects beyond your immediate field. This will help you spot trends and patterns that could impact your strategic goals.
4. Embrace and Manage Risk: Adopt a calculated approach to risk-taking by evaluating the potential benefits and drawbacks. Learn from both successful ventures and failures to refine your strategy over time.
5. Value and Plan for Contingencies: While appreciating the importance of planning, also prepare for uncertainties. Develop scenarios to navigate potential future changes and disruptions.
6. Engage in Thoughtful Debate: Create environments where debate is encouraged, and diverse perspectives are valued. Use such discussions to challenge your own assumptions and refine your strategic thinking.
7. Expand Your Network: Seek relationships with individuals who are known for their strategic insights. Regularly engage with them to discuss trends, challenges, and opportunities.
8. Stay Informed: Keep abreast of global and industry trends that can impact your strategic direction. Use this knowledge to adapt and align your strategy with external changes.
9. Articulate and Share Your Strategy: Clearly communicate your strategic vision through a well-crafted narrative that resonates with stakeholders. Regularly review and adjust the narrative as your strategy evolves.
10. Innovate Continuously: Commit to lifelong learning and self-reinvention. Be open to experimenting with new ideas and approaches, and avoid becoming complacent with current successes.
11. Leverage Strategic Tools: Utilize strategic frameworks and tools such as SWOT analysis, PESTLE analysis, and Porter’s Five Forces to structure your thinking and decision-making process.
12. Reflect and Journal: Through journaling, reflect on strategic successes and setbacks. Document insights and lessons learned to inform future strategic decisions.
13. Align Actions with Strategic Intent: Regularly evaluate your tasks and initiatives to ensure they align with your strategic objectives. Prioritize activities that have the most significant strategic impact.
14. Practice Patience and Persistence: Recognize that strategic results may not be immediate. Stay committed to your long-term vision and be prepared to adapt as circumstances evolve.
15. Encourage a Strategic Culture: Build a culture that rewards long-term thinking and strategic initiatives. Encourage your team to think beyond day-to-day operations and consider the broader impact of their work.

These steps aim to foster a deeper, more comprehensive approach to strategic thinking and action. Try integrating these practices into your routine to enhance your team’s capacity.

If you made it this far, thank you for the time you took to read my musings. I hope this material is useful for you or someone you know.

Best of luck in your endeavors!