The Power of Left Field (Questions)

The Power of the Left Field

When I was a little kid growing up in what is now Silicon Valley I developed a habit of asking a lot of questions - both in school, religious education and everywhere else. I am sure I was one of those annoying kids that would ask his parents numerous times a day – WHY???

So no surprise that when I first became a manager of people, I did not stop asking questions but rather turned my habit into one of my super powers.  Sure, I asked some of the standard questions that managers ask in the general one on one sessions -- but I would often ask something totally unrelated to the primary purpose of the meeting or what was accustomed in the standard process of a typical meeting on a topic. 

Why did I do this? Was it because I lost my mind or could not stay focused on the subject or primary purpose of the meeting – Hardly! Everything I did was purposeful I was trying to get an unrehearsed answer, the truth, an actual state of the union, or to make the point that I was watching things that maybe people thought I was not. 

So how did this work?  Let’s take a few examples. 

·     The Sales Forecast Call:  In a typical forecast call managers ask about the status of the quarter by rep or leader on a deal by deal basis. I would do the normal stuff…start with the deal, next steps, the economic reason why the deal was going to close, who needed to approve, etc…. I would start at the biggest deals with the highest probability to close (normal practice) but very quickly I wanted to take my team on a journey of their forecast. I would ask questions on deals that were forecast in the quarter but were deep down the forecast probability, had not been updated, and sometimes even deals in the next quarter… Why? To run an enterprise sales team at scale I needed to instill a sense of ownership of everyone on my team that our forecasting system was reliable and always up to date.  By calling on the deals that everyone else forgot I was teaching my team that I had not forgotten and that it was critical that they knew the latest on everything  --  even the accuracy of deals in out quarters. 

o  Small note – I did light a few people up that did not have strong command of their business. It was never personal it was always business, and the expectation was that world class teams understood the details. I am sure a few @Datadomain and @Servicenow people will comment. 

·     The 1:1 Casual Conversation with reps or employees either at lunch or in their car between meetings. These conversations often focused on a business issue, prepping for a meeting, but also included getting caught up on our various lives outside of the office. These people were my “WORK FAMILY” and they matter to me. But then I would add something different – Tell me the last time you got coaching from your manager that you thought was valuable? What would your dream job be at the company or any company in 2 years?   In both situations I would get surprisingly honest answers… if I got an answer to the first question “when was the last time you got valuable coaching from your manager” I would often get answers like – I am not sure or we don’t meet regularly. You can imagine that set me down a path to make sure we were enabling managers to be coaches but also would usually get me to say something to the employee that included… I hope you know that coaching is a two-way street. If you don’t feel like you are getting the help you would like, please seek out your manager and ask for more feedback. 

The dream job question was also incredibly revealing. First many employees don’t get asked what they want to achieve in their future and as such they believe that their company and leaders don’t care about them. Second by asking we can then engage in an entire coaching /feedback conversation about what they need to focus on to be ready for the next step(s) in their career.  This question has allowed me to recommend folks for many different experiences that they would never have been exposed to if not for an interested leader spending a few minutes to ask the question. 

·     The Customer / Prospect Questions: As a sales professional I was trained to ask all types of qualifying questions and learned the art of spending more time listening than I did talking. One of my favorite questions that I would ask to executive near the end of the meeting (after we have done the usual work to validate the value and the business case for change, etc… ): What is your favorite / most valuable business relationship you have with an outside company that provides services/technology to you? How did it become your favorite? 

What am I trying to do by asking this question? 

First most people must think about an answer for more than a beat… but then you get the “meat” of how you can make sure that you build your relationship on the foundations of what is most important to your clients.  It was surprising how varied the answers would be from people of a similar role in a similar industry (Don’t assume anything). 

Typically, my customer teams were in these meetings, and I would make sure to tell my team members that the next time I ask that question to this customer I want them to say our company (Insert company name).   

(Now as an investor I ask this question to the founder / CEO’s -- who is your favorite board member, advisor, I am not asking because I am always able to achieve that goal but good to know the high water mark and to make sure I think I can understand what this person values – Am I a good fit? After all this will be a long-term relationship.    

Asking great questions sometimes -- especially the ones that seem out of left field enable you to achieve your goals and aspirations.  Be curious... Good luck on your path toward excellence! By the way I was not good enough in baseball as a kid to play left field…it was right field for me.