Are You Thinking Like a Challenger?

5 min readOct 18, 2021


This post originally appeared on Entrepreneur.

Eight steps to approach entrepreneurship like a Challenger.

If you know the story of David and Goliath, you already know what it means to be a Challenger. As a tale of thinking differently to overcome seemingly insurmountable competition, it’s an important lesson for today’s entrepreneurs.

Rather than being defined by their size or the industry they’re in, Challengers fight smarter and with purpose. They look at different ways to identify and master their unfair advantage, and balance long and short-term goals that actively use capitalism to benefit society and the environment.

Being a Challenger is a mindset, a way of life and a playbook to view the world around you. Here are eight steps you can take to ensure you’re approaching entrepreneurship like a Challenger.

1. Be your own customer

Buy and use your own products or services. Anonymously experience your own customer service and take it a step further by dedicating a day a quarter (at least) to responding to customer service requests. Doing so will deepen your understanding and build empathy. In what ways does your product or service fail, meet and exceed expectations? Where are you vulnerable relative to existing and emerging competitors? What will it take to be exceptional and what are you going to do about it? Consider extending this practice to the entire executive team, or a more diverse group of voices and experiences, and compare notes.

2. Walk in your competitor’s shoes

An integral part of thinking like a Challenger is understanding the competition so you’re better positioned to displace it. That doesn’t just mean relying on market research and Google reviews. Go out of your way to get a true sense of what it means to live like your competition. Buy and use their products, consume their marketing and social content, anonymously call their customer service to get a sense of their experience, documenting your joys and frustrations along the way. Consider who they are speaking to and who they are leaving out, the needs they are addressing well and failing against, and whether they are advancing society and improving people’s lives. Use all of this data to identify opportunities where you can do better, address unmet needs and change the game.

3. Embrace negative customer reviews and feedback

Receiving negative feedback about your brand is never a pleasant experience, but it’s often founded on truth. Dedicate time to practicing social listening and scouring relevant review sites. Take what someone is saying to heart and see whether there are patterns emerging with other negative feedback. Not only that, but negative reviews are damaging. Embracing and addressing negative feedback today will positively impact your long-term value.

4. Seek out analogs

If you monitor your industry and nothing else, you’re living in a silo. Challengers study disrupters and those upending the status quo in other sectors, be that music, art or something else entirely, in the hopes it can be applied to their own industry. Think of it like sampling in music, where you take something that already exists, that’s familiar to the listener, but you reimagine it so it becomes part of a completely new recording. This is the basis of many new business models where disrupters aim to be the Uber of X or the Patagonia of Y. Consider how these new business models and innovations apply to your business and industry.

5. Establish a challenge network

In his book Think Again, Wharton School professor Adam Grant introduces the concept of the challenge network. This network is a team of critics, outsiders and creatives you surround yourself with who question assumptions and consistently push you out of your comfort zone. They are, as the book describes it, “a group of people we trust to point out our blind spots and help us overcome our weaknesses.” Every Challenger Brand and Challenger thinker should have a challenge network, or be actively in the process of building one. Start with a group of four provocateurs you can convene to review your strategic plan or product road map, and consider meeting with the group (or a subset) with greater frequency to help you anticipate competitive threats, errors in judgement and/or capitalize on new opportunities.

6. Stage debates

As well as creating a challenge network, you should ensure you’re fostering an environment where debate is healthy and your team feels comfortable taking sides on the existential threats facing your business. Be it committing to a decision that moves your model from one that’s product-based to service-based, rigorously debating how your approach can be more sustainable or how your company can be more inclusive, you want a team and an environment that can uncover new ideas and ways of thinking. As part of this, actively stage debates to push people to advocate for a side and, in the process, learn from opposing or different positions.

7. Experiment

The greatest Challengers are those that embrace experimentation. Google still uses the 20 percent rule it famously shared in 2004, wherein it encourages employees to spend 20 percent of their time working on what they think will most benefit Google. It’s something that empowers them to be more creative and innovative, but is something that should be introduced to your processes. This can be institutionalized through hackathons that force time away from your core business and allow competing teams the time to conceive of and develop new ideas, or by setting up a skunkworks team to work on new ideas. These ideas are likely to fuel joy, build innovation muscles or even generate revenue. Allowing time to think outside the box and foster experimentation will yield dividends.

8. Know this isn’t about you

If there’s something that defines a Challenger Brand it’s their focus on wider impact, be that on society or the environment. All of the above should empower you to advance your business while advancing society and the planet. More than ever, consumers are aligning with brands that share their views. Studies show that 83 percent of millennials want companies to align with their values and 76 percent want CEOs to speak out on issues they care about. Brands have a responsibility to double down on their political position, and speak out about moments that move them. Don’t shy away from this. Embrace it. This is what leaders do and what the world needs.




5&Vine is a Marketing Agency and Fractional CMO for Challenger Brands.