Business tips from a strategist and reality TV host

Misti Cain, host of the new series Werrrk!, shares what every business leader should know to get ahead

Everyone loves a good reality makeover show. From Queer Eye to Extreme Makeover: Home Edition, so many television series showcase the excitement of a turnaround story—the “before” pictures of an old, falling-apart apartment and the “after,” typically a pristine new home. But how does this model apply to a struggling business? Werrrk!, a new Mailchimp original transformation series, is proving to be not only applicable but also educational and entertaining.

In season one of Werrrk!, three experts (the WerrrkForce) confront struggling small businesses. Their goal is to bring order to chaos by overhauling management styles, bonding teams, and redesigning workspaces. One of the experts, Misti Cain, is also the show’s host and a founder of Whyzze, a business strategy company. Whyzze helps entrepreneurs create step-by-step profit, process, people, and productivity business action plans. 

Cain sat down with WeWork Digital Labs for a conversation about business makeovers, and provided her top tips on management, strategy, and mentorship. 

Here are her top five business tips:

1. Ask why

Cain chose “Whyzze” as the name of her business strategy company because she believes in the importance of asking why (especially if you have a spaghetti brain of mixed-up thoughts, ideas, and tasks, or if you have decision fatigue). Ask yourself all the “why” questions you can think of, for example: Why do something? Why choose that direction? Why didn’t something work as expected or fail? Why is a question that helps us focus toward a solution. A good book on the topic is Start With Why by Simon Sinek.

2. Treat prioritization like triage

When prioritizing tasks, treat it like an ER. Ask what’s hemorrhaging and what is OK overall. If you’re facing a crisis (or a “bus crash”), you need to triage. Moments like this can be overwhelming, so look back at your company mission statement. Remind yourself of your team’s core purpose to help identify where to place your focus first.

Cain recommends reading this Medium article by Benjamin Hardy, which has one framing question for dealing with crises: “Will it make us go faster?” If you measure your decisions by this one single question, it will be easier to say yes or no.

3. And then slow down

Prioritization problems means you don’t know what should be focused on versus what should be left off the plate. This can lead to burnout for yourself and your team. As a TechStars mentor, Cain believes in the saying “Do More Faster,” but sometimes it is best to slow down and focus on one task or initiative at a time so you and your team can understand the results and effectiveness of what you just accomplished. 

4. Specificity is key internally and externally

Internally, properly defining your team’s roles and responsibilities is critical to ensuring there’s no waste through duplicative work. Clear titles help people understand and own their responsibilities and the results of their work. If you’ve hired employees as generalists, make specific delegations that take advantage of their unique skill sets. 

For businesses in the consumer space, building the right design and outward-facing customer experience is critical. If you work in retail, for example, design your shop in a way that will help visiting customers clearly understand what you are selling. Using deliberate signage or separating your store into zones will focus your visitors’ attention and expectations.

Whatever strategies you employ, you must test them over and over again to ensure they work for your business. 

5. Mentorship is a two-way street

When finding a mentor, note three things: First, understand your specific challenge. If you don’t, you won’t be able to identify a mentor with the appropriate experience to match your needs. Second, don’t come to a mentor with a question you can Google. Do the basic work first and then come with follow-up questions. And lastly, give back to your mentors. Even if you feel like you have nothing to give, small actions like liking, commenting, and sharing their content or brand can go a long way in showing you appreciate them. And always keep them in the know about your progress after they’ve helped you.

Misti Cain is the founder of Whyzze (pronounced “wise”), a business strategy company. Cain is also the host of business reality show Werrrk! by Mailchimp Presents, an all-star mentor for Techstars, and an executive in residence for Cal State University, San Marcos. Her passion is helping the workforce love Mondays.

Osnat (Os) Benari is head of WeWork Labs, leading its digital and content experience. Before joining WeWork, she headed partnerships for BBG Ventures and headed product innovation and led the product groups for AOL Video and Studios.

Interested in workspace? Get in touch.