5 Day Plan For Being an “Undercover Boss”!

April 2, 2010

I have become fascinated with the program Undercover Boss, as it is amazing what the bosses learn from going undercover. Of course, it is a bit difficult to go undercover as a boss in a 5-100 person company when you have interviewed and/or spend time with everyone and each person already knows every other person in the company. So what does an expansion stage boss do to get more detailed insights into his/her company?

Here is my model week for the Expansion Stage Undercover Boss:

Start by getting into the right mindset. You are not the boss of the company this week, but rather an inquisitive new person that wants to learn as many different perspectives on your company as possible. Then, introduce your plan to your senior team and appoint someone to take care of your day-to-day duties for the week.

Day 1: Become a customer service staff member for a day. Get on the phones, answer e-mail, get on the web chat system, and really find out what your customer issues are and what your company is doing about them. There is nothing like customer issues to help you understand the product and development issues, people issues, and process and system issues that you have. Write up your key insights at the end of the day.

Day 2: Call several prospects that you have lost to competitors for a full day. There is nothing like talking to a prospect that you have lost to really understand why they purchased a different product to help you better understand what you could be doing to win more customers (be careful, though, as you want to make sure that you are talking to prospects that you are targeting, as other prospects may lead you in the wrong direction. Also, be careful that you don’t take one response and generalize it). Any loss could be a product and development issue, as sales issue, or an influencer issue and getting to the bottom of your issues is the starting point of continuous improvement! Write up your key insights at the end of the day.

Day 3: Spend a full day with a salesperson. There is nothing like a day with a salesperson to truly understand the issues and opportunities in sales and marketing as well as product and development (note: you need the full day to really get a solid understanding, so don’t turn this into an hour). Write up your key insights at the end of the day.

Day 4: Spend a full day with users of your product. If you have a lot of users at a single location, go to that location. If you can invite users in for a day, invite them into a “user feedback day.” If you can’t do that, call your users for a day and ask them about their job, how they use your product in the context of the job, and what they see the issues and opportunities being. Again, it will generate a lot of great product and development ideas. Write up your key insights at the end of the day.

Day 5: Reflect on the week and the insights for the week. Then summarize your thoughts on what you heard and consider the options for what you think that the company should do differently. Clearly, your week is not a statistically significant sample, but if you can’t figure out at least 5 things that you are sure that you should be doing differently then you are not trying very hard (you should get a list of at least 100 items, many of which need to be investigated further are lower priority, but 5-10 should be obvious adjustments that someone should be implementing). Then, determine the best way to have an impact on your company with each of the items on your list, by grouping them into three categories, “should change now”, “should research further”, and “should make a backlog item”.

At your next meeting with your senior staff, give them your findings, conclusions, and recommendations and ask for help making some changes and putting other items on your backlog.

Spending a week out of your day-to-day rhythm is a huge investment, but doing it will give you a much better understating of your company and its issues, your customers and their issues, and will also help you to understand your customer service and sales staff, the two functions that have the most contact with your market.

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.