Interview with Chief of Staff Expert Founder, Tyler Parris

Written by vChief

January 8, 2019

Our frequent partner and collaborator, Tyler Parris, who runs and wrote a book on the chief of staff role is offering an intriguing new professional development opportunity for people in the chief of staff role. Maddy took some time to interview Tyler about it.

Maddy: So, Tyler I hear you’re launching a chief of staff mastermind group this year. What prompted you to do this?

Tyler: I created in 2016 to be a community where chiefs of staff come together to find content and resources, share knowledge and information, and to be the portal through which that community found each other.


What I’ve learned over the past couple years is that online forums are great for transactional kinds of sharing: Who has a project management tool they love and what do you love about it? Or, what do you think of the latest strategic planning app? Or, I’ve been asked by my exec to set up a comms function from scratch and I’ve never done that before – help!

But the real value of our community has been in events like our Chief of Staff as Leader

or Managing Conflict Before It Manages Your Leadership Team workshops, where people actually come together and can go to the next level of depth describing a challenge they’re having, that they’re not going to talk about in a LinkedIn group, and the answer for which they can’t simply Google.

Where you can feel isolated as a chief of staff, the mastermind group is a year-long learning cohort or 12-15 chiefs of staff that combines the power of chief of staff-specific training, group & 1:1 coaching, and peer advisory to create community, connections, and continuous learning. Mastermind cohorts are the next stage in the evolution of that community.

Maddy: What kinds of topics will you cover in the cohort meetings?

Tyler: I do have some content based on my research and common challenges that chiefs of staff face, like getting role clarity, leading from behind, systems and strategic thinking, preventing negative surprises, managing rhythm of business, or managing conflict and team dynamics. And, the beauty of this cohort model is that the cohort will tell me what they’re dealing with, and we’ll wrestling with those issues in real time.

Maddy: You and I both know that chiefs of staff are busy people. Will they commit?

Tyler: As of this writing, we’re already at half-capacity for the first cohort, so yes. Today’s top and emerging leaders make time for development in areas that are important to them. I realize not everyone works for an executive who supports them in this kind of work, and not all chiefs of staff are great at drawing boundaries around their own time or prioritizing their own development. The mastermind cohort is about prioritizing your own development, having a safe space to wrestle through what you need to wrestle with, practice what you need to practice, and to ask and be asked the incisive, powerful questions that stretch you.

Maddy: And there’s a cost to attending?

Tyler: Yes, and I’ve priced it less than a typical grad school course but more than a commoditized training because it’s context-specific to the chief of staff role, there’s research and expertise that I bring, value in the learning from each other (even I learn new things from chiefs of staff time we have an event!), and honestly people who have skin in the game are more engaged. Finally, I’d say that people who’ve attended our workshops in the past put things into practice that demonstrate return on their investment.

For example, it takes the average CEO-chief of staff tandem 9 months to get clear on how the role adds maximum value. That’s a long time for the leadership team (the “staff” in chief of staff) to be confused about who’s doing what, how the role functions, etc. and that drag diminishes the exec’s credibility. If you can shorten that to 3 months or less, how valuable is it? Or, chiefs of staff report on average spending 4 hours/week managing unhealthy conflict (higher than the average American worker at 2.8 hours). That’s a lot of time defending turf and building alliances while projects get delayed and good people are leaving because of the toxic environment. How much is it worth to deliver projects on time, keep good people, and proactively manage that conflict before it festers? The answer is different for everyone, but it’s a no-brainer.

Maddy: where can people go to find more info or sign up?


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