Frequently Asked Questions

Every Chief of Staff role is unique, but some common job responsibilities include:

• Process development and improvement.
• Change management and implementation. 
• All Hands, Team Offsite, or similar large event planning.
• Program or project management, especially involving senior leaders or cross-functional teams.
• Executive communications, PR, ghostwriting, speechwriting, slide creation, etc.
• Establishing meeting agendas, sustaining team focus, recording and following up on action items.
• Creating executive scoreboards, dashboards, goals or OKRs, plan-on-a-page, etc.
• Team engagement, development, camaraderie, transparency, fun, etc.
• Telling leaders and peers "the kind truth" and helping them grow, improve, and adapt... for the good of the whole team or organization!

Watch the video: What (exactly) is a chief of staff, anyway?

Frequent client requests include:

• Research - competitive, peer, industry, etc.
• Leadership off-site or All Hands planning
• Workshop or Team-Building - Event Design & Facilitation
• Engagement Survey action planning, development activities
• Team & Leadership Development - activities, workshops, exercises, coaching

Think about the leader they'll be supporting. You want to find candidates who:

• share many of the leader's strengths and mindsets -- this is essential for them to become a "right hand" to and proxy for that leader, in due time, 

and

• fill a leader's gaps -- common needs include: empathy, patience, clarity, organization, people skills, approachability.

Also, Chiefs of Staff tend to come in one of two molds. You'll need to ask questions to find the "type" that's right for you. Do you want a Chief of Staff who...

• Type 1: speaks on behalf of their leader, and who is seen as an extension of that leader, 

or

• Type 2: stands for the whole team and organization (including the leader), and will challenge members of the team (leader included), for the greater good.

(I have a strong bias toward Type 2, but there are situations and leaders for whom Type 1 tends to be a better choice.)

Watch the video: Which flavor of Chief of Staff is right for you?

Recruiters & Leaders: Want more personalized advice? Book a time.

Be vocal about your interest in becoming a Chief of Staff, especially to your current manager or the senior leaders and executives within your network.

Look at your current and prior work experiences. What tasks are you already performing--or have you already performed--that are often listed under "chief of staff" duties? See the list above, to spark ideas.

Redesign your resume, cover letters, and LinkedIn profile to highlight those experiences. 

• If you have a close relationship with a former manager, reach out and ask if they would be comfortable with you adding the designation "Chief of Staff" to your job title, since you held many of those responsibilities. (For example: "Communications Strategist | Chief of Staff" or "Executive Assistant & Chief of Staff")

Look for opportunities to take on more "chief of staff" responsibilities, within your current or next role, so that you feel confident and prepared for your next move, which is...

1. Ask to be promoted (or title changed) to Chief of Staff, in your current organization, or
2. Apply for Chief of Staff roles, within other teams or organizations.

Invest in yourself: See if a Chief of Staff Coaching Package is right for you.

Bloom where you're planted. Look for opportunities to "up-level" anything you're asked to work on, and volunteer to take on work that's more strategic than what you might be assigned. 

(For example, if you support a Chief Marketing Officer and are asked to plan the annual leadership retreat, you might ask if they've considered making it a Go To Market Leadership Retreat that includes Sales and other related leadership teams. If they're open to that idea, offer to take the lead on bringing everyone together and building the agenda.)

Be vocal with the leader you're currently supporting, and make it clear that you're looking to grow in your role. Tell them you want to become a thought partner and true "right hand" to them, as a leader. Ask for feedback, and accept it as a gift.

Create the time and space for more advanced, valuable work, by paying close attention to how you're currently spending your time and energy. Look for ways to make time-intensive, repeatable activities--such as All Hands preparation--run more smoothly. 

(This is what business leaders often refer to as "operationalizing" something. Make it simple, mistake-proof, and easy to hand that task to someone more junior, who will benefit from the chance to work on something new!)

Invest in yourself: See if a Chief of Staff Coaching Package is right for you.

Yes: 

1. Subscribe to the Chief of Staff Coffee Break newsletter, and 
2. Check out the Coffee Break video playlist.
3. Consider a Chief of Staff Coaching Package.

Sure. I offer several coaching packages that may be a good fit. But if you're looking for just a one-time, quick advice call, feel free to schedule a 1:1 Coaching: For Chiefs of Staff, current or prospective.

Yes. Of course you can. It's not rocket science, silly. :)

Maybe. It depends on a few factors:

How long is your financial runway? Aim to have at least 6-12 months of living expenses in the bank, so that you aren't stressed about making your rent or mortgage payments. (If you're unemployed and your runway is short, it's wise to explore both new job and freelance opportunities.)

Will you enjoy running your own practice, more than being employed? That's hard to say. It's worth finding out the answer, by giving it a go. You can always find another job, if you don't love it.

Look for existing professional relationships that you can tap into. It's helpful to find an "anchor client" to give you a small amount of steady business, while you build more. Often, this comes from someone you've already worked with, in the past. Focus on cultivating your network. Make clear what kind of work you do, and be open about the fact that you're taking on new clients.

Start small. With all new clients, suggest starting with an engagement or preliminary phase of a project that will be low risk for everyone. Getting the initial budget commitment is nearly always harder than continuing or expanding an engagement when things are going well. So make it easy on everyone. Agree to a few weeks of part-time hours, and test the waters together. In most cases, this will bring clarity for both parties, as to whether working together will be mutually beneficial. 

Don't get lost in the details. You can figure it all out, as you go along. I promise. Google is your friend, here. Eventually, it's a good idea to: 

• establish a basic website (I use GoDaddy), 
• start paying quarterly estimated taxes (I use QuickBooks),
• set up an LLC business entity (great free advice available from LLC University), and
• set up a business checking account (I use Chase).

Yes! Suggested resources: 

• Grow Your Independent Consulting Business - a podcast by Melisa Liberman
• Getting Naked - a great book (with a terrible name) about client service, by Pat Lencioni

First and foremost, recognize that price is rarely the sticking point, if you're having trouble closing deals. Most business clients just aren't that price-sensitive. They either want your services and are ready to spend money... or they're not. 

(If they want to work with you, they'll counter-offer or try to find a path forward. So don't sweat it too much!)

But with that being said... I have done freelance work for many years, and when I was first getting started, my pricing methods included:

• Ask my Magic 8 Ball - "Cannot predict now."
• Ask other consultants if $X seems like a crazy number - "I dunno. It's probably fine."
• Google to see what others charge, and realize no one who does what I do, actually discloses that info
• Throw a number out and see if the client recoils in horror (Note: This indicates nothing.) or cackles with delight (This indicates you're probably undercharging.)

These days, I use somewhat more scientific methods:

1. Take my estimated annual compensation when employed in a similar job (salary, bonus, stock, 401k match, benefits, etc.) and multiply by 1.5 (to account for overhead costs, self-employment taxes, administrative work, billing, etc.)

2. Divide that number by 2000 (approximate number of full time working hours per year). Round up to get my hourly rate.

3. Multiply by 8 to get my daily rate or by 4 to get my half-day rate.

4. Consider which rate will be most sensible for the project or client. (Usually half-day is best for my type of work.) 

5. Make an estimate of how many hours / days / half-days the given request will require. Add 10% more, because I tend to under-estimate. Ask myself if I've factored in edits and changes, rescheduled meetings, indecision, delays, etc.

6. Track my time religiously--including hours spent thinking about the work, rescheduled meetings when I can't recoup the time, etc. This helps me get better at estimating, and prevents me from low-balling my bids.

Suggested resource: 

• How Independent Consultant Rates and Retainer Fees Work is an overview of different pricing models (value-based, hourly, retainer, etc.) and can help you think through your options.

Signs your prices are too low include:

• You are earning less per hour or per year than you did as an employee, for more effort and hassle.

• You have more requests for work than you can deliver, but you can't afford to hire anyone else to help you.

• Your clients happily sign their first deal, but then try to low-ball you on future work. (This indicates that you've differentiated yourself on price, and you're presenting yourself as the equivalent of the fast-food value menu, which is a race to the bottom that you'll never win.)

Signs your prices are too high include:

• Your prospective clients can get similar services, at a similar quality, with similar ease, for significantly less money--and they continually choose your competitors.

I've found that if you are easy to work with, and you deliver excellent results, clients will consistently choose your services, without much regard to cost. (If you don't do both of these things, clients will be reluctant to work with you, even if you lower your prices.)

Nope. I'd rather start working with the client immediately, so we can see if the relationship will be a productive one. 

I have plenty of good ideas, and I'm much more afraid of committing to the wrong project or client, than I am of "giving away" one or two ideas! 

If taking 30-45 minutes to brainstorm initial concepts together ultimately helps us both decide whether we want to embark on this work together, that's a much better use of my time than putting together a formal proposal. 

Plus, when it's time to talk numbers, my bid will be much more accurate, because we've done that initial discovery work.

• Credit for this approach goes to Patrick Lencioni and his approach to client service, which you can read more about in Getting Naked. 
• I also learned it by observing one of Pat's incredible consultants, my friend and mentor Kevin Twomey.

Not much! Most of my business comes from existing clients or their referrals. Beyond that, I have...

1. This website and the blog. 
2. The (very) occasional LinkedIn post. 
3. A few proposal templates that I can easily pull together for some of my repeatable services, or adapt here and there. (I usually send these as a follow-up, after we've both decided that we'd like to work together.

It's fastest and easiest for me to just use the client's standard Scope of Work or similar documents. I usually request their paperwork, fill it in (and flag anything I'd like to change), and take things from there.

In general, my approach is to lead a trust-based business. That means I'm slow to engage with a new client, as I want to observe how they do business: 

• Do they pay on time? Net-30, Net-60, ahead of schedule, require prompting, "the check is in the mail," etc.
• Do they value my work? If they want to secure my availability, they will pay an upfront deposit. 
• Am I being reasonable and fair? If they've paid for work in advance and then don't need it, I look for other ways to contribute, regardless of the Scope of Work. I aim to be flexible, no matter what the contract says, if their dates slip.
• Is this relationship working for both of us? If not, I'd rather walk away, even if I'm leaving money on the table. 

I try not to put either myself or my clients in the business of owing large amounts of money, for long periods of time. Billing early, often, and in steady increments, tends to mitigate risk for everyone.

Sure. I do not provide ongoing business coaching, but I understand that sometimes it helps to get some quick advice, validation, or a nudge to get up and going! 

If you'd like to talk with me, please schedule 1:1 Coaching: For New Consultants or Freelancers.