What if the key to startup success isn't always unwavering confidence but occasional and thoughtful strategic ambivalence? Each approach has its merits.
There's risk in both overthinking strategy and rushing into action. However, when making pivotal decisions, you can use ambivalence to explore options before executing with confidence.
Let's take a confident look at ambivalence.
Ambivalence as a Strength
Ambivalence means seeing the benefits of multiple options. It makes you more receptive to new information and diverse advice. You can better understand and empathize with the positions and perspectives of multiple stakeholders.
Holding ambivalence is also valuable in these situations:
Strategy – viewing all options to mitigate risks and optimize outcomes
Creation – exploring new features, reaching markets, or increasing efficiency
Negotiation – empathizing with others to find mutually beneficial results
Organization – weighing all threats/opportunities for the company & team
Ambiguity can feel uncomfortable as you evaluate multiple choices and weigh their risks while feeling pressure to act. If you can sit with that discomfort, however, you'll likely find the best options.
When you demonstrate ambivalence as a leader, your team will seek input from each other, become more collaborative, and resolve problems faster.
Ambivalence as a Weakness
Ambivalence can be detrimental in certain situations:
Emergencies – when you must decide and act quickly
Implementations – when you must focus and execute efficiently
Conflicts – when you must defend your company or team determinedly
Deadlines – when you must move forward decisively
Another concern is that deliberating and seeking advice may be perceived as weakness or incompetence.
𝗪𝗵𝗲𝗻 𝘁𝗼 𝗞𝗻𝗼𝘄 𝘁𝗵𝗲 𝗗𝗶𝗳𝗳𝗲𝗿𝗲𝗻𝗰𝗲
By understanding the strengths and weaknesses of both approaches, you can consciously choose which to use.
The situation and audience should guide whether you respond thoughtfully or decisively. For example, you should rely on confidence when pitching potential investors but embrace ambivalence when brainstorming with your team. Negotiations can benefit from either approach, depending on the disposition of the other party.
For pivotal decisions, ideally you can discover options through ambivalence and then execute one with confidence.
Julia Hartz, CEO of Eventbrite, talked about how the pandemic upended their growth:
"There's a paradox in leadership
of being decisive and being curious...
the learnings were coming fast
and in big waves."
However, she had to take immediate action despite information unfolding in real-time. That’s to say effective leaders appreciate the powers of ambiguity and confidence.
Brian Chesky, co-founder of Airbnb, demonstrated the power of ambivalence when facing early challenges. In 2009, Airbnb was struggling to gain traction. The co-founders were confident in their core vision but remained open to feedback and pivots. This ambivalence led them to realize their initial focus on providing shared space with air mattresses and breakfast was too narrow. They expanded their concept to include entire homes, allowing people to comfortably and affordably travel more, and leading Airbnb to exponential growth.
In another example, Sara Blakely, founder of Spanx, showcases how confidence and ambivalence can coexist. Blakely was confident in her product idea but ambivalent about the intricacies of the fashion industry. She spent nights and weekends learning about hosiery, patents, and manufacturing. This openness to learning, combined with her unwavering belief in her product, allowed her to navigate challenges and build a successful company.
Dwelling too long in strategy and leaping too quickly into action both carry risks. One effective approach is to evaluate your options for a defined period and then agree that everyone must support the final decision.
Key Takeaway: By understanding the value of both ambivalence and confidence and choosing between them deliberately, you expand your range of possibilities.
Want to Practice? Spend 5 minutes (yes, right now) to consider one big decision and determine if ambivalence or confidence (or both) is the right approach.
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90% of startups fail. Build Scale Grow solves problems for fast-growing startups, specializing in Social Impact, EdTech, and Health Tech and focusing on Introverted Founders.
I wrote this post with AI editing. Photo by Niklas Hamann who can be found here.
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