A Leadership Story: Training Context

by Matthew Richter

Picture this: A client calls you up and asks if you can design and deliver a customized training program on Having Difficult and Assertive Conversations. Your first reaction is, “Of course…” But, your more responsible and likely reaction is to ask, “What problem does a Difficult Conversations class solve for you in the business?” Or some variation of that. Your client says that the Board feels women haven’t been promoted as much throughout the company and they strongly believe this is because women don't know how to assert themselves as strongly as men in the business. A good workshop would help fix that. This is where many of us would stop. Many of us would stop asking about the business problem and begin looking for skill gaps and uncovering program logistics. But, the real questions here should be, “Why does the board think a Difficult Conversations class will solve the problem of women not getting promoted?” “What data are the board referencing when it says women aren’t getting promoted as much?” “Why does the board want more women promoted?”

Our inclination, our habit, or our tendency is to allow our own needs (to get a gig with a client) and our own assumptions (I know why the board wants women promoted and how a Difficult Conversations class can help that) fill incomplete gaps in actual knowledge of the context. We jump to our conclusions because we want the job. Reasonable enough, but to what effect? How successful can our training intervention actually be just based on assumptions we make about the situation?

More to the point, why does the board think their proposed approach is indeed the solution? I know from experience I will design an excellent conversation program where participants will overwhelmingly rave about their experience. But I also know the client will never run an efficacy study to evaluate whether the program really increased promotions among women.

As designers and trainers, we embrace the known. And when we aren’t familiar, we insert our own contexts and perspectives to fill in the blanks. We don’t ask lots of questions about how our program connects to business issues because in part, we know if we do, we will talk the client out of hiring us.

Training context involves the following, probably incomplete list:


  • Participants
  • Managers
  • Stakeholders
  • The Training Team
  • You
  • Your Competitors
  • Anyone Else Involved


  • The Business Issues
  • The Problems
  • Resources (Or lack of…)
  • Policies and Principles
  • Events and Actions
  • Locations and Their Localization Effects
  • Knowledge & Skill Gaps


  • Corporate Values & Beliefs
  • Style Preferences of People
  • Personal Values & Beliefs
  • Current trust among people
  • Experience of the people
  • Current Climate

Before we make a recommendation to solve a problem, we need to assess and understand all of the components in the above table. Before you bite my head off and laugh at me, arguing this will take forever, remember, I believe in rapid instructional design and doing my assessments concurrently with my training design. Understanding the training context need only take an hour or two of thoughtful conversation and observation with the parties involved.

I will never be able to fully mitigate the impact my own personal filters will have on my interpretation of what is happening, but the more I can derive as comprehensive an understanding as possible, the more my perspective will hold legitimate and useful weight. And, paradoxically, I still believe my experience and ability to read business situations has helped make me successful. You, too. So, it is okay to trust your gut. Trust, but verify.

Your perspective forms from the different ways you may interpret the context. Your perspective is a filter—but it is a filter you have built over your career. Use your perspective to frame a story for your client that describes both your solution and how your solution will solve the problem. The more your story resolves an actual problem and still addresses the concerns they initially came to you with, the more likely they are going to hire you. You must be able to tell the story in a way that resonates with the client. Your story must be clear, focused on their needs, and still fixing what you actually think is wrong.

Given the Difficult Conversation example I started with, perhaps through exploration, we will come up with clarity about the real issues worrying them and develop a solution that address those, instead of a hastily identified conclusion based on intuition.

Don’t just settle for the “Can you deliver for me…?” request. Dig deeper. Understand more. Learn the context, know your story and tell it.