As I transition my career to focus more on consulting with startups and agencies, I’m discovering patterns in my discussions with business owners. My OCD/anal-retentive nature drives my need to identify, organize and communicate new discoveries once again. This time around, I was inspired by the classic “5 Ws” of strategic planning: Who, What, When, Where and Why (and the How too) and how they translate to building a successful startup.

Overall, business owners follow predictable patterns of behavior. As mentioned in an earlier article, The Three F’s Every Successful Entrepreneur Should Master, a majority of entrepreneurs start a business based on intimate knowledge of a discipline (copywriter or architect) and find themselves in a new role (business owner) at which they are not proficient. This leads to a host of challenges, as you might imagine if not personally experienced.

The objective behind identifying and outlining the 5 W’s of a Successful Startup is to ensure unseasoned entrepreneurs avoid common traps and costly mistakes. Those of you who have experience growing a small business should be able to provide specific strategies or tactics you’ve implemented for each of the topics below. For the rest of you, consider this the framework of a future exercise.


What is the purpose of your business? Why do you get up in the morning and go to work? Is it the same reason as the rest of your employees? Can your customers and partners verbalize or at least understand your purpose? If you’re unable to answer this question easily, or the answers vary significantly among stakeholders, I suggest scheduling a meeting or offsite to explore further. At the end of the day, everyone invested in your company should have consistent if not cohesive agreement on purpose. Otherwise, the dissonance can shake the company apart.


How are your customers? Where is your market? This can be rhetorical or tactical in nature. For example, your market may be a geographically-oriented retail business or it could be a global social media platform for professional photographers. Regardless, you should have a clear understanding of your market, down to the ideal customer (persona or archetype). Consider a team exercise where you create a collage (if not shrine) to your target customer (what they eat, drink, watch, listen, etc.). Market segmentation is okay, but there should be common elements that connect across markets (sense of humor, level of intelligence, common pain point, etc.).


Now that you’ve identified your ideal customer, what exactly are you asking them to purchase from you? What problem are you solving? How does your solution differ from competitors in the marketplace? What are current and future threats? Are there opportunities to adapt your solutions to meet evolving needs? The objective is to hear your employees and customers to be able to accurately and consistently describe the benefits of your products or services. If you can’t do it, how do you expect to build a successful sales and marketing program?


Perhaps the most critical of the W’s, the Who refers to your team. Who is going to live the mission, vision and purpose every day, leading the company to its overall strategic end game? Assess your current team’s personalities, talents, Freak Factor and map them against future needs. Do you have the right people on the right seat on the bus? What additional training or professional development is required to round out skills and knowledge? What external talent will need to be added to the mix? Designing a consistent corporate culture is essential to attracting and retaining top talent, so ensure you are proactively creating a work environment that fosters your core values and purpose among the team.


As I’ve discussed in an earlier article, having a vision of the future, specifically an exit plan, is critical. Are you looking to sell the company? Go public? Step away from the company and have the team manage it for you? Regardless of your desired exit strategy, you need to start thinking about the long term now, and reverse-engineering milestones to ensure you map to your target on time.

Bonus: How

Last but not least, what is your go-to-market strategy? Are you a sales-driven organization? Do you rely on PR buzz or word-of-mouth referrals? Most companies prefer a well-rounded mix of sales & marketing strategies to maximize reach and revenue. That said, every company has a unique DNA that drives the company, from strategic decisions to tactical actions. What is your strategy? How is it different than your competitors? Is it sustainable? Will it get you to your end goal? If you’re not sure, let me know and I’ll put together another article on the subject.