Best Practices For Operations, Chief of Staff, and Generalist Roles — Founder Handbook

WRITTEN BY: UPSIDE PARTNERSHIP

We wrote up some best practices from our experience running hiring processes for chief of staff, operations, and generalist roles.

General

One of the most helpful resources we have used while running a process has been a book called Hiring For Attitude by Mark Murphy. The general idea behind it is that attitude is a much bigger issue than skillset when it comes to hiring. The author found that 89% of bad hires are attributed to attitudinal reasons (lack of coachability, lack of emotional intelligence, motivation, etc). Many of the best practices below are drawn from this book.

While this is a good guide / framework, there are certain exceptions. These exceptions map directly to what the operations role looks like for your org, your expectations of the person in that role, and if / how you hope that person will grow within your company. For example, after hiring people with various skillsets and experience, we believe attention to detail is a crucial strength of a great candidate, and one that is difficult to fully learn on the job. It’s absolutely possible for someone to improve in that capacity, but the difference between someone who is naturally very much on top of everything, and someone who is trying to force organization can be like night and day. Similarly, the skillset of thinking multiple steps ahead, or second-order thinking, is a vital skill the best operators / chiefs of staff / general athletes have mastered.

We recommend making a list of the non-negotiable things you need from someone coming into this role and make sure to check that list throughout the interview process. That list is your true north.

Designing a Great Process

Before kicking off an actual process, make sure you’re clear on what you’re looking for (see above). Make a list of the qualities that high performers at your company have (and / or what you expect from high performers coming into the company). Then, make a list of qualities that do not fit your culture. Ask your teammates for their opinion on these as well. What do they think works well and what doesn’t?

Then, think through the questions you want to ask during an interview. Pick questions that pair well with the high performer qualities you’re looking for (and / or the qualities you’re trying to weed out). For example, if a high performer never says, “that’s not my job,” then ask a question like, “could you tell me about a time when you were given an assignment that really didn’t fall within your role?” You’ll get interesting answers for this for roles like COS, since the responsibilities are often vague, cover a lot of ground, and vary greatly.

”Stay away from vague or leading questions that show how to gain a desired response.”

The way you frame questions is important. Stay away from vague or leading questions that show how to game a desired response. Don’t ask hypothetical questions- candidates will usually give you an idealized answer. Similarly, un-differentiating questions (like the last two in the list below) won’t give you useful data. Every interaction and question you ask in an interview should give you an actionable data point.

Stay away from questions like:

Tell me about yourself
What are your strengths?
What are your weaknesses?
Tell me about a time when you had to balance competing priorities and did so successfully.
Tell me about a conflict with a coworker and how you resolved it.
What would you do if...?
How are M&Ms made?
If you could be any animal, what kind would you be?

Try to drill down for specific examples whenever you can. Instead of having to sift through surface level responses, this allows you to get specific data points (What exactly did that candidate work on? What exactly happened? etc).

Good example questions:

Could you tell me about a specific instance?
Could you tell me about a specific instance where that person led by example?
Tell me about a time you lacked the skills or knowledge to complete an assignment.
Could you tell me about a customer you found particularly difficult to work with?
Could you tell me about a time when your manager gave you an assignment that didn’t seem to make much sense?
Could you tell me about a time when you were given an assignment that you were sure wasn’t going to succeed?
Could you tell me about a time when you were struggling to meet a commitment you had made to a customer or colleague?
Could you tell me about a time when you were given an assignment that really didn’t fall within your role?
Could you tell me about a time when working across departmental, divisional, or regional lines was challenging?
Could you tell me about a time when you had to think outside the box?

Note: These are also relevant for reference checks!

Assessing Coachability

Go through the following five points in order (if it applies- you’ll have to customize this if you obviously know the candidate’s previous manager- like if that person was the one who introduced you). This is meant to produce honest, thoughtful responses.

What was your previous boss’s name? Please spell the full name for me.
Tell me about [name] as a boss.
What’s something that you could have done (or done differently) to enhance your working relationship with [name]?
When I talk to [name], what will he or she tell me your strengths are?
All people have areas where they can improve. When I talk to [name], what will he or she tell me your weaknesses are?

Responses to the second point in this list can indicate self-awareness. High performers tend to have high levels of critical self-awareness. You can also get a sense for if and how the candidate demonstrates a sense of ownership. This is vital for an excellent generalist.

Things To Look Out For

According to Mark Murphy, high performers and low performers use different language. Here’s the breakdown you can use for reference. It gets pretty nitpicky, but it’s just a good thing to read and be aware of. The general takeaway is to pay attention to how each candidate speaks in your interviews.

Pronouns

First person pronouns: high performers more frequently use first person pronouns (~60% more). I, me, we.
Second person pronouns: low performers use far more second person pronouns (~400% more). You, your.
Third person pronouns: low performers use ~90% more third person pronouns than high performers. He, she, they.
Neuter pronouns: low performers use 70% more neuter pronouns than high performers. It, itself.

Verb Tense

Past tense: high performers use 40% more past tense answers than low performers.
Present tense: answers from low performers use 120% more present tense than answers from high performers.
Future tense: low performers use 70% more future tense than high performers.

The takeaway here is that high performers will tell you about something that actually happened / something they did. An example of a story about something they accomplished, etc.

Emotions

Positive emotions: high performers use ~25% more positive emotions (ex: happy, thrilled, excited).
Negative emotions: low performers use 90% more negative emotions than high performers (ex: angry, afraid, jilted, pessimistic).

Qualifiers

Adverbs: low performers give answers that contain 40% more adverbs than answers of high performers (ex: quickly, totally, thoroughly).
Negation: low performer answers use 130% more negation, such as “no,” “neither.”
Waffling: low performers use 40% more waffling than high performers in answers (ex: maybe, could be, perhaps).
Absolutes: low performers use 100% more absolutes than high performers (ex: always, never).

Projects

When you have late stage candidates, you may want to give them a brief project or two to test for skills that are hard to suss out during a verbal interview. If you choose to go down this path, make sure the project will give you the type of data you’re looking for.

For example, if you’re hiring an EA (or having someone do scheduling work as a core component of their role), giving that person an example screenshot of 1-2 weeks of your calendar is a good start. You could then ask that person to do a scheduling / prioritization exercise to see how they make decisions, organize themselves, and think. For a chief of staff, some example projects we’ve seen are below.

Give the candidate a video or presentation and have them write an analysis. We’ve seen processes where candidates were given a video of a company exec giving a talk and were asked to critique it. Many people simply gave a glowing review: “this was great, that person is so smart, she / he did a great job.” What would have stood out was if a candidate would be direct and upfront with an opinion. An ideal response would have highlighted areas where the talk could have been elevated, what could have been better, and some other commentary on the topic.
If a candidate will potentially be working across a few teams, consider giving them an exercise that highlights his or her ability to work collaboratively. Maybe this is a scenario you lay out for that person and have him or her walk you through the approach he / she would take. Do they include things like, “first, I’d ask what our end goal is. Then, I’d reach out to person A on team X and find out what work has already been done here and if there’s any context I need”?
Is there a specific task that you already know will be given to whoever fills this role? If it doesn’t require a ton of institutional knowledge, it could be a great way to see how a candidate would tackle that. Provide any details needed to get the job done reasonably. Using a task you already have a framework for is helpful when it comes to analyzing how candidates perform. You probably have already thought about it and have a baseline for how it should be done.
Ask a candidate to walk you through the steps for something they know how to do very well. It could be about anything- the subject itself doesn’t matter. This is a good exercise to see 1) interpersonal skills, 2) communication skills, 3) attention to detail, 4) attention to and orientation around process.

Think about what is most essential in the role and mirror the exercise to that.

Other

It’s helpful for broad operations roles to give candidates a sense for what they can take on and how they can grow within the organization.
Once you do hire this person: the more insight and transparency you can give this person, the better he or she will do. Think of great chief of staff as being the other half of your brain. He or she should know you and how you work well enough to seamlessly take things off your plate- trust between the two of you (and whoever else this person supports) is essential.

Originally Published: October 1, 2019
https://www.upsidevc.com/#rise-together

Hiring For Generalist Roles