The Art of Context Switching

By Brett Keirstead, FCSO, FCRO

After a long career as a Full-time Sales Executive across numerous organizations, in Feb 2023 I made the leap into the Fractional world as a Fractional Chief Sales Officer with Chief Outsiders. There were many reasons I did this, but one was the fact that I found myself getting bored quickly in a single organization. I thought, I love learning about new things and Fractional leadership exposes you to all kinds of new ideas.

But I didn’t quite understand what that meant in reality. What I now realize is that the most challenging aspect of Fractional Leadership is undoubtedly: Context Switching.

Certainly consulting has been around forever and in those roles consultants move in and out of projects, sometimes with multiple at the same time and have to juggle ideas, timelines, and deliverables, that often cause confusion. For me though, what I have found to be different in a Fractional Leadership role is that often you function in an ‘Operating role’ not just part of a project team.

Practically, as a Fractional Chief Sales Officer, what that means is I am responsible for the day to day management of the team (i.e. individual Salespeople) and I operate an Executive with financial accountability for performance goals. What you bring to that table is more than just advice or work product, but actual leadership, management, and day-to-day interactions across a myriad of subjects and circumstances.

And you have to be present and fully engaged in all of them.

For example, let’s say I operate as a Fractional Sales Leader for 4 different firms. Each of the businesses is between $5M - $20M in revenue across 4 unique industries (i.e. Telecom, Fleet Care, HR Tech, and Staffing). And each of those organizations have 2-4 Salespeople along with a CEO that I have to report into.

In these Operator roles, to be effective you need to check in with your team nearly every day to help them move along deals, provide strategy and learning moments, review forecasts and other reporting. In addition, to communicate you must engage with numerous different tools (Google Suite, Teams, Slack, GoTo Meeting, Salesforce, Hubspot, etc). There are individual meetings, team meetings, strategy sessions, and Executive meetings

Keeping all this straight is incredibly complicated and mind consuming. In the course of one day I may have to engage with all 4 clients in some fashion, each time having to ‘context switch’ in my example it would be between HR Tech, Fleet Care, Telecom and Staffing. Some sell to mid-market, some enterprise - some sell licenses, some are services. It’s incredibly complex.

I admit I am an ideas person and not an organized person so that has added the challenge. I implemented Calendar Bridge to help me keep my meetings straight. I also try desperately to end meetings 5 minutes early and if possible keep 30 minute gaps in between. I have a map of the US up in my office so I can see where all the companies are (states and time zones) and a white board that shows all my main contacts, their color coding, and what the most pressing issues are. I have individual school spiral notebooks for each client all coded and labeled. That has helped with the organizational skills.

The context switching is a different story.

When I worked for a single company, the flow of topics and ideas was fairly linear. There were slight variations based on the nature of the event but if it was an HR Tech company selling SaaS to mid-market, at the end of the day that grounded most discussions. In Fractional Sales Leadership, it’s ‘like a box of chocolates’ - you never know what you will get.

What has been the key to solving this: morning daily preparation. I have scheduled my day (the nice thing about Fractional is you can) so that the first 30 minutes is reserved for ‘Context Prepping’. I look at all the key meetings I have for the day, and write notes about key topics, the individuals involved, issues we are working on, and my desired outcome. I then scan those before every meeting just to put me in the right frame of mind. It helps with jargon and what specific clients use for common terms (i.e. Leads vs Opportunities, AE vs SR, ARR vs ACV, etc.). The language of every client is very different and the burden is on us to adapt.

It gets even crazier when you start thinking about Company Culture. One company might have a more modern culture where dress is very casual (i.e. baseball caps) and language is more relaxed (cursing may even be acceptable) and in the next meeting people dress more like a corporate environment and swearing is grounds for termination. One CEO may be a visionary and the other a task master. It’s very difficult to keep it all straight.

Has this been hard? Incredibly. Have I messed up? Absolutely! In fact, very early on I mentioned a person from the wrong company to the CEO of another client and he said ‘sorry, who are you talking about?’. When you work for one firm you can often ‘wing it’ as there is a natural cadence from meeting to meeting. The people stay constant and you can develop a rhythm easily. In a Fractional World you are constantly switching. At the end of a full day of meetings covering 4 clients across multiple industries, you are mentally exhausted. But for me, also exhilarating.

So if you are considering a Fractional Leadership role with multiple clients be prepared to tackle this challenging but rewarding topic. Do your homework, take care of your physical health, get organized, drink water, have a standing desk, keep good notes, be present, and pay attention.

Context switching is hard but you can do it! And it sure beats six hours of wasted meetings and the constant distractions of working in a single office for single company. I'll take context switching with four companies over stuck in one company any day. There are also tools to help you get really good at Fractional. Try my friend John Arms Fractional Bootcamps or get to Frak 2023, the first Fractional Conference in the US coming this fall. (Right in my home state of Minnesota)

Brett Keirstead is a long-time member of Voyageur U and a Fractional CSO for Chief Outsiders. He is based in Savage MN and is the author of the book We Are All Sales, People. He hosts the Salespeople are People Too podcast on Spotify that shares real world successes and struggles of everyday sales people.