Great question! I tell people that Chiefs of Staff help run an organization but without the C-suite money or glory. I say it with humor, but it’s true. The role of a Chief of Staff is fluid and customizable, and can even shift between leaders and/or levels of organizational maturity. But, at its heart, the role is meant to smartly and strategically support a leader in extending themselves into their organization. I’ve written a two-part, in-depth primer about the role, which you can read here and here, or access a downloadable copy of here.
Yeah, there are! Some of the industries benefiting the most from Chiefs of Staff are healthcare, education, and the non-profit sector. I contend that Chiefs of Staff can make an impact in any industry, and in businesses and organizations of any size and any maturity level.
Another great question! I tend to think the biggest difference between a Chief of Staff and a Business Manager is the entity to which they primarily provide support. Chiefs of Staff are meant to primarily support a leader (or multiple leaders), while Business Managers are meant to primarily support the business, agnostic of leadership. I created a simple chart to help clarify the differences between a Chief of Staff, Business Manager, and Executive Assistant, which you can find here.
I am an accredited OBM (Online Business Manager) through OBM School, but I don’t market myself as one because I don’t think the title fits me all that well. My experience is as a Chief of Staff. I prefer supporting leaders and leaning into business management where and when it makes sense. While I am a doer, I prefer to work more frequently at a strategic level, and do so in organizations of varying sizes, types, and sectors. To me, the OBM role feels more niche and execution-oriented (which isn’t to say strategic thinking isn’t part of their skill set because it is). Don’t get me wrong! There is absolutely a market for OBMs, and there are some insanely talented OBMs out there; I just don’t hang my hat on that title. If you’re looking for an OBM, OBM School has a robust directory of service providers.
I’m working on a resource that addresses this in detail, with info like which questions you should ask yourself and business metrics you should look at to help guide your decision. But, here’s the short of it: You may never feel “ready” to hire a Chief of Staff because we tend to greatly undervalue the impact of support roles, both in our personal lives and in business, making it harder to see the positive financial impact of them. And, for better or worse, we’ve defined success at the cultural and societal levels with financial metrics.
That being acknowledged, if you are on the cusp of a significant growth phase, or if you’re getting ready to build out a team, or if you’ve had an unexpectedly stellar year and are unsure how to invest some of that back into your business, a Chief of Staff may be a good hire. Essentially, if you’re on the precipice of a big shift in your business and/or leadership responsibilities—or, heck, your life outside of work!—and worry about doing it alone, a Chief of Staff may be able to help. There are other ways to know, too; these are just a few top-of-the-noggin thoughts that come to mind. More to come on this one!
If we haven’t worked together before, no. In fact, our agreeing to a retainer is contingent on completing a Strategic Consult together. And here’s why: the Strategic Consult gives us an opportunity to experience how the other person thinks and works, and experience how we’ll work together, without a longer-term commitment. That 90-day plan I hand to you at the end is yours to do with what you will, and there’s no requirement for you to continue working with me afterward if we’re not a fit. It simply benefits and protects us both to ensure we’re a good fit before entering into a longer-term agreement.
This is a one-time fee and activity—if you invest in a retainer and, at the end of it, decide you want to keep working with me, you don’t have to do or pay for another Strategic Consult. And I greatly appreciate your desire to make a longer-term investment, which is why I provide the Consult at a steeply discounted rate.
To some degree, yes. I work in 3-month increments for quarterly planning purposes, and I do have a minimum retainer length of 3 months—to ensure there’s time to get familiar enough with your business and processes—and a maximum length of 12 months, which are non-negotiable. But if I’m coming into the middle of your quarter or there’s a specific project you’d like me to work on that doesn’t quite fit into the 3-month-interval framework, I can work with that.
I typically charge on a monthly basis, and invoice at the end of each month with 30-day net terms. If you need a different payment approach or extended net terms, I am absolutely open to discussing that and facilitating what I can within reason.
For now, I don’t offer the ability to pay through my website because I have concerns about being able to securely facilitate substantial payment transactions, and I still need to complete my research to validate or invalidate those concerns. If I was selling lower-priced goods or services, it would be less of a problem. That being said, I don’t want my payment process to be burdensome, so, as mentioned above, I am exploring different processes and may make payment through my website possible at some point.
From time to time, I may offer a specific, limited-time discount for certain services (for example, a discount on annual planning workshops in September and October). When I do so, I will have specific messaging on my website and in my marketing materials saying so. I also offer discounted rates to clients for referrals.