Finance & Operations

Become an Undercover Boss in 5 Days

September 6, 2010

What better way to understand how your company runs and what impact your decisions have on employees and corporate structure than to infiltrate the ranks and discover what it’s like on the ground level?

S is for Superman

That’s what happens on the CBS show “Undercover Boss.”  Executives learn about the inner workings of their companies by becoming employees themselves.  The results are dramatic and eye-opening—but of course, that’s reality TV, and we know how “real” that can be.

It’s especially hard to become an undercover boss in an expansion stage company where your employees know who you are and what you do—but it’s not impossible.  There is a way for you to learn what they do on TV in just five days. Here’s how.

First you have to set the stage, and that starts with your mindset.  Think of yourself not as an executive but as an inquisitive new mind approaching a corporate situation from various perspectives.  Be sure to tell your senior management team your plan and designate someone to handle your daily tasks for a week—you don’t want them thinking you’ve lost it and vanished.

Also, be sure to keep a daily log of everything you learn during your experiment.  If all goes according to plan, you ought to garner a lot of valuable information by the end of the week, and you’ll want those notes handy when crafting future directions.

Day One: Become a Customer Service Staff Member

Get on the phones, respond to e-mails, engage with your organization’s web chat client, and really delve into your customer issues head-on.  Your customer service team knows better than most what issues your group is facing; they field complaints, suggestions and—if you’re lucky—praise.  Begin to understand product and development issues, people problems, and the process and systems snares you face.

My colleague Tien Anh Nguyen wrote a piece about text mining—the process of deriving high-quality information by analyzing your customers’ feedback on various channels, especially social media.  Adding text mining to your day, or perhaps after your day as a follow-up step could strengthen what you learn.

Day Two: Call Prospects You’ve Lost to Competitors

By day two you should have a firm grasp on what issues affect your customer base.  Crank that up a notch by engaging with lost client prospects.  Discover why these individuals chose your competitor’s product over your own.  Much like day one, day two will give you a ground-level perspective of what you should be doing to win more customers.

Be careful with this part.  Focus on prospects that are still in line with your target segment—speaking with prospects that are not in your target segment may lead you in the wrong direction, as their interests, not running parallel to your target prospects, could inappropriately change your focus.  Also be wary of taking one or two responses and generalizing the information.  The more lost prospects you engage with, the more data you’ll have to analyze and categorize, painting a more thorough portrait of what is causing your losses.  Getting to the bottom of these funnel leaks—whether they’re due to a product and development issue, a sales problem, or an ineffectual influencer—is the starting point towards continuous improvement.

Day Three: Shadow a Salesperson

Not only will a day shadowing a member of your sales team give you a unique perspective of how the process works, it’ll open your mind to potential future marketing opportunities and custom sales strategies.

Don’t skimp on day three—it’s important to spend the entire day with a member of your sales team, and not just a couple of hours.  If you choose to become a part of the sales process itself, it may give you the chance to lead by example, overhaul the way your lead generation team functions, and debunk myths about how sales work.

Day Four: Shake Hands with Your Product Users

Day four allows you to step outside the confines of your office and connect with the heart that pumps blood into your organization: the users.  Sure, your group developed the product, but what do you really know, outside of market research, about how your product is being used?

There are multiple ways to get hands-on experience with your users.  If your product is used in a specific location, go to that location, meet the “regular people” who rely on your wares, see what ideas they have about future product development.  If you can’t conduct face-to-face meetings, call your users, ask them about their jobs and how they use your product in that context.  Or, if neither of those opportunities is possible, set up a “user feedback day” at your company and allow your user base to talk about there experiences with your whole product.

Day Five: The Day of Reflection

Compile the notes you’ve taken throughout the week and structure them so you can have key takeaways from your experience.  Consider the options for what you believe your company should do differently.  What are your weak points?  What are you strengths?  Understanding both will help you craft a detailed roadmap going forward.

Clearly, spending one week jumping from role to role isn’t going to provide a statistically significant sample, but you should have at least five to ten areas where you need to be doing something different.  If you don’t have the bare minimum, you didn’t try hard enough.  Ideally you’ll have a list of 100 items requiring further investigation, many of which will be of lower priority, but five to ten should be obvious adjustments that someone should be addressing.

Organize your findings in three categories: change now; research further; and turn into a backlog item for future development.

Once you’ve gathered your vital information, it’s time to present it to your senior management team.  Ask your team for help making changes, prioritizing tasks, and developing the best strategy for continued advancement.  Becoming an undercover boss is great for any organization, but is most useful in the expansion stages, as it will promote development and improvement when and where it’s needed most.

It’s not easy stepping away—even temporarily—from your executive position and reintegrating with the bone structure of your organization.  Even a couple hours away from e-mail can bloat your inbox.  But by becoming an undercover boss, you’ll learn more about your company and your customers with their respective issues.  Better understanding your customer service and sales staff, and how they function, is also vital—they’re the ground-level customer-facing employees that can make or break your organization.

So clear your calendar—it’s time to delve into the guts of your company and truly understand every grinding gear.

Founder & Partner

As the founder of OpenView, Scott focuses on distinctive business models and products that uniquely address a meaningful market pain point. This includes a broad interest in application and infrastructure companies, and businesses that are addressing the next generation of technology, including SaaS, cloud computing, mobile platforms, storage, networking, IT tools, and development tools.