I wrote a colorfully-named post years ago called Onboarding vs. Waterboarding, which detailed out some of the general principles around onboarding new employees that our companies have used over the years. A few weeks back, one of our clients and fellow CEOs of a Series C Ed:Tech company asked me for tips on onboarding senior executives, and some of what I said varied from or built on that earlier post.

Here are a few of the themes we riffed on:

1. Treat the new hire onboarding like you would a merger integration. Why? Well, because adding a new exec to your company is kind of like…a merger integration. Make a long checklist. Assign each item an owner and participating parties. Have a weekly meeting with all key stakeholders specifically to review the onboarding plan. In other words, don’t just leave it up to you, the new exec, and a Day 1 overview meeting with “business as usual” check-ins. Make it its own thing.
   
2. Take great care to communicate expectations and changes internally when the new exec starts. Any new exec, but especially one in a newly-created or upgraded role, will carry a new role description which by definition changes expectations and responsibilities both of the new exec’s role and of other execs’ roles (and possibly your own role or Level-2 team members’ roles). Make it super clear to the organization both in a meeting and in writing what those changes are. If people used to go to you for X, and now they have to go to New Exec for X, don’t leave that to the guesswork and imagination of your team.
   
3. Get out in front of the fact that your exec team has changed. As I always say, any time you change one person on a team (add or subtract), you have…a new team. Treat a new exec onboarding as such, though this will take time. Team dynamics will change, and you need to drive that process. You also need to make sure any shared language and tools on the team take a beat and include the new person. Did you run a DISC or use Myers-Briggs two years ago with your exec team? Great, do it again with the new team. Did you do a major trust/vulnerability exercise at an exec offsite last year? Better do a new one from scratch. This may sound like extra overhead, but it’s worth it. You don’t want the new person to always feel like the new person who is missing an inside joke. Plus, those kinds of things are always good hygiene for exec teams.
   
4. Begin with the end in mind. On Day 1, your new exec won’t know where the bathroom is, unless you are an all-remote company of course. Your objective is for the new exec to be just as autonomous as all other execs ASAP. So, work backwards from 90 or 180 or some other number of days on the question of autonomy. Build this into your integration checklist and weekly integration check-ins (see above), but note this is also a mental evolution both you and the new exec (and the rest of your exec team and the new person’s direct reports) need to go through. Some areas will be more logical for the new exec to be autonomous on Day 1 or at least Month 1. Some will take longer. Be explicit about defining those things.

Special thanks to my friend Amir for inspiring this post!

This is the second post in the series…. the first one When to hire your first Chief People Officer is here).

While all CXOs are important to a company, the Chief People Officer is the one role you don’t want to get wrong because People Ops impacts every facet of a company. If you hire the wrong people—even one wrong person—you’ll regret it, and so will everyone else in your company. If you short-change the onboarding process you’ll create tons of work for others in the company to answer questions, teach people the systems, and help them get up to speed quickly—not to mention the frustration of the new hire. And of course, if you or your employees do anything illegal, discriminatory, or harassing, you’ll end up in legal trouble and you’ll lose—big time. So, it’s not enough, if you’re expanding rapidly, to “just get a Chief People Officer,” you need to hire a great Chief People Officer and I have found that great Chief People Officers do three things particularly well:

The most important characteristic or attribute of a great Chief People Officer is that they believe their function is strategic. In Startup CXO Chief People Officer Cathy Hawtrey wrote about the ways in which HR/People can be a strategic function and not just a tactical corporate function.  It’s true of most functions, but for whatever reason, (likely past experience), HR leaders frequently don’t view themselves or their functions as strategic, which is not only a huge missed opportunity but maybe says something more important about the confidence level of the Chief People Officer.  If that’s their frame of reference, then they will likely be tactical managers, they’ll keep the trains running on time, but you won’t be able to anticipate the changing talent landscape, much less be strategic about it.  If they believe they can move the needle on the business by improving engagement and productivity and efficiency, if they believe they can make the executive team more effective by helping you with team facilitation and coaching…they can do anything.

A second important characteristic of the Chief People Officer is courage—they have the courage to call you (you, the CEO) out on things directly and firmly when they see you doing or saying anything that is a bit off. It could be around language, inclusion, values, authenticity, or anything else, but they don’t let it slide or ignore it. The CPO, along with you, are the principal stewards of the company’s values and culture.  Even the best CEOs benefit from having a watchdog from time to time.

A third critical trait of a great Chief People Officer is that they think about investment in People in terms of ROI.  It’s one thing to run a killer recruiting function and fill seats efficiently, with high quality, as asked.  It’s an entirely different thing to start the recruiting process by asking if the role is needed, at that level and compensation band, or whether there are other people, fractional people, contractors, or shifts in lower value activities that could be put to work instead.  Only heads of People with deep understandings of the business can transform the function from a gatekeeper/”no” role into a business accelerator.

A great Chief People Officer is all of these things—strategic, courageous, and financially astute. Above all, great Chief people Officers know that they are the role model within a company and that their behavior, their language, their inclusiveness is setting the tone and providing a template for others to follow. 

(You can find this post on the Bolster Blog here)

I’m fascinated with this topic and how it’s evolving in society. In Part I, a couple years ago now, I changed my long-held point of view from “CEOs should only wade into politics when there’s a direct impact on their business” (things like taxes and specific regulations, legal immigration) — to believing that CEOs can/should wade into politics when there’s an indirect impact on business. In that post, I defined my new line/scope as being one that includes the health and functioning of our democracy, which you can tie to business interests in so many ways, not the least of which this week is the Fitch downgrade of the US credit rating over governance concerns. Other CEOs will have other definitions of indirect, and obviously that’s ok. No judgment here!

I am a regular viewer of Meet the Press on Monday mornings in the gym on DVR. Have been for years. This weekend, Chuck Todd’s “Data Download” segment was all about this topic. The data he presented is really interesting:

As I said in Part I of this series, “I still believe that on a number of issues in current events, CEOs face a lose-lose proposition by wading into politics,” risking alienation of customers, employees, and other stakeholders. The data from Meet the Press supports that, at least to some extent. That said, I also acknowledge that the more polarized and less functional the government is…the more of a leadership vacuum there is on issues facing us all.

(Post 1 of 4 in the series of Scaling CPO’s)

In most startups, the HR function starts out as tactical, because you have to get people hired and paid, and while you might have a founder or early-stage employee who can do these things, often these tasks are frequently outsourced to a PEO.  As the company grows, it probably in-sources payroll and benefits, hires a recruiter, and maybe has an HR Manager who handles the function. Depending on the number of roles you see being filled, the degree of specialization, or a host of other factors, an in-house team to handle the tactical aspects of HR makes a lot of sense. But at some point you may need to hire a Chief People Officer.

One sign that it’s time to hire a Chief People Officer is if you feel that you’re the driver of company values, that you’re the one talking about values and viewing the company and interactions with that lens—but you’re the only one that cares about the core values. If your HR function is only focused on the tactical aspects of the role and not on how values drive the company, you’ll need to consider a full-time People Officer because focusing on tactical functions only will not help your company scale.

Another sign is if you are spending too much of your own time training managers and leaders or working on interpersonal dynamics on your leadership team. What’s the right amount of time? I think of these tasks (if you’re a a CEO) as things where you should be more like a consultant rather than the driving force behind them. If you find that a large portion of your day or week is filled with people ops activities, it’s time to think about hiring someone.

A third sign that it might be time to hire a People officer can happen when your board asks you what your talent strategy is with respect to improving diversity, retention, and engagement metrics, while simultaneously decreasing average employee salary, and you don’t have a great answer. While it’s acceptable—occasionally—to not know the strategy at a detailed level for a particular part of your business, if you get asked a question by your board and haven’t the faintest idea on how you can get an answer, that ‘s a good sign that you should consider brining in a full-time Chief People Officer.

A fraction Chief People Officer may be a great option, especially if you have a very competent HR manager or director who has strategic inclinations but not enough experience operating as a strategic executive.  If you have a person who just needs a little more supervision in order to “level up” then a fractional executive could be helpful. Or, if you need someone to play more of a consigliere or team coach role to your executive team but don’t want to engage a coach — and your day-to-day HR leader is getting the job done but too junior to facilitate workshops for the senior team, a fractional executive would work. Finally, if you have a very junior HR function or are insourcing it for the first time and need help setting up the whole function from scratch at an advanced size relative to other functions, a fractional executive would be helpful.

As a startup it’s easy to focus on the day-to-day operational details of the People Ops team because those things—payroll, benefits, hiring, onboarding—are tangible and have metrics associated with them. But those things won’t help you scale. If you want to scale your company, if you want to go from $2 million in revenues to $50 million you’ll need to have a person in your organization who is passionate about the values and passionate about helping individual contributors and leaders connect their work to the values. A Chief People Officer will be able to step in and be a leader to the leadership team; after all, companies are built into greatness by people, so this key position is pivotal to the company. 

(You can find this post on the Bolster Blog here)

I hosted a CEO roundtable dinner the other night, and someone in the group asked me what my favorite question was to ask in interviews. I kept thinking about something I read years ago, that the late legendary Zappos founder Tony Hsieh used to ask, “do you consider yourself a lucky person,” about which he said, “Lucky people approach the world with an open and optimistic mind that enables them to see unexpected opportunity more readily.“

That’s a good thing to find in a future team member of course, but the question is a little too indirect for me.

My favorite question (ok, it’s a compound question) is to ask someone “What are you great at? What do you absolutely love doing, what gets you out of bed in the morning? And what’s the intersection of those two things?”

In terms of an interview question, it’s one that’s hard to game and also one that gets someone talking authentically about themselves in a way that you can use to evaluate both their cultural fit and their role fit.

This also happens to be the approach I take when I’m giving someone career advice. Think through those three things, and you should start narrowing down the kind of job you want to go after.

Years ago, I heard then General David Petraeus give a talk to a small group of us about leadership. He was literally coming to us live from his command center in Iraq or Afghanistan when he was running the whole theater of war over there. I realize he subsequently had some tarnish on his reputation after pleading guilty to a misdemeanor around handling classified information, but the main thrust of his talk, his Formula for Strategic Leadership, still stands as one of the more memorable talks on leadership I’ve ever heard and is no less relevant as a result.

Given that I still remember it vividly 14-15 years later, I thought I’d recreate it here with my own annotations after the four principles. It’s a simple 4-step formula:

1. Get the big ideas right. Obviously, you aren’t going to go down in history as a great leader if you consistently get the big picture wrong. That doesn’t mean you have to be right about everything and every detail. But if you pick the wrong market, bet on the wrong approach, happen to get your timing wrong by a few years…it’s hard to win.
2. Communicate them up and down the organization. Every mature leader knows that ideas and plans only go so far if they stay in your head or get filtered down through leadership teams. For your values to take root, for your strategy and strategic choices to make sense, and for people in the organization to be able to connect their daily execution to your company’s north star, you need to spend a lot of time communicating those things throughout the organization. Different groups, different meetings, different channels. And then, when you’re finally exhausted and sick of hearing yourself say those things over and over and over again…keep saying them.
3. Personally oversee their implementation. Leaders who throw things over the proverbial wall — “here’s what to do, now go do it while I move on to something else” — are not really strategic leaders. The devil is in the details. If you can’t bother to spend a few minutes overseeing the implementation of your strategy and carefully watching when and how it works and doesn’t (see next item), you may be a good visionary, but you’re not really a strategic leader.
4. Memorialize and institutionalize best and worst practices. This is where so many leaders fall down on the job. When something in your organization wraps up — a launch, a quarter, a project — you have to do a retrospective, curate learnings both good and bad, and publish them. That way your whole organization can have a growth mindset as a system.

There are about a zillion books on leadership out there. Most of them are probably between 200 and 400 pages long. While they may all have variations on this theme and colorful examples behind them, this still rings true for me as the essential formula for strategic leadership.

This was a catchy title I caught in our shared Kindle library at a moment when I wasn’t connected to wifi and had nothing to read. Thanks to Mariquita for buying it…it was a good read.

The book is funny, irreverent, and deep. It speaks a lot about pain and failure and how those can help create resilience. It is also chock full of great anecdotes including a particularly memorable one about Pete Best, the original drummer for the Beatles who got fired by the rest of the band on the eve of their becoming famous.

Here’s one particularly representative quote:

Pain is an inextricable thread in the fabric of life, and to tear it out is not only impossible, but destructive: attempting to tear it out unravels everything else with it. To try to avoid pain is to give too many fucks about pain. In contrast, if you’re able to not give a fuck about the pain, you become unstoppable.

Every founder would benefit from reading this book. It won’t stop you from giving a f*ck about everything (it can’t), but it might give you a couple tools for not giving a f*ck about some things, which would clear up some mental capacity for other more important things!

People talk a lot about Imposter Syndrome — “What am I doing here? I’m not qualified to do X at all” regularly when it comes to women and people of color in the workplace. That is a real thing. It shouldn’t in any way be discounted. It’s painful to go through and painful to watch.

I’d guess that 9 our of 10 founders have Imposter Syndrome at least once during their founder journey. Maybe it’s even more like 99 out of 100. And I bet most of them have it more than once…some regularly. This may be even more true for founders from underrepresented populations, but it happens regardless of demographic.

Being a founder is inherently unnatural. Seeing the world through a different lens, inventing something, and being crazy enough to act on it, quit your job, raise capital, and convince other people to quit their jobs to join you on your journey is a tall order no matter who you are.

No founder’s journey exists without speedbumps and moments where things aren’t working and you feel like your company is going to die a horrible and painful (and worse, public) death – what my former Board member and friend Scott Weiss famously calls the WFIO moment (We’re F’d – It’s Over), popularized by Ben Horowitz in The Hard Thing About Hard Things.

Founders, it’s ok. We’ve all been there. Take a step back. Solve the problem. Change the approach. You’re not in the wrong place. You’re just having a bad moment. And most important, remember, you’re not alone.

Post 4 of 4 in the series of Scaling CPO’s- the other posts are, When to Hire your First Chief Privacy Officer, What does Great Look like in a Chief Privacy Officer and Signs your Chief Privacy Officer isn’t Scaling.

There are a few high-quality ways I’ve typically spent the most time or gotten the most value out of Chief Privacy Officers over the years. Part of it may have to do with the business we were in at Return Path (and now, Bolster), but part of it is understanding what the Chief Privacy Officer needs from the business and working with them in that arena.

For example, I found it helpful to work with the Chief Privacy Officer to help them to deeply understand our business.  Part of what I think we got right in this regard at Return Path was that we almost always made this a fractional role that was combined with other responsibilities — Tom Bartel, Dennis Dayman, and Margot Romary almost always did other senior jobs in operations or product as well.  This is what most likely enabled us to play more offense with the function rather than play defense. Even with an operation or product background, the Chief Privacy Officer is typically focused on external threats and issues and I have found that working with them on business issues not only raises their knowledge, but helps them understand potential security risks.

Another thing I did was to role model training and compliance.  If you mention of the word “compliance” to just about anybody in the organization, you’ll see that it doesn’t usually get anyone’s juices flowing. But it’s important for the company to live up to its obligations with customers and with its own internal policies and we found that if we involved a certain amount of employee training every year around compliance, we were able to build skills and stay on top of changing dynamics.  I always try to be the “first done” on an online training course and make sure to follow related policies so that our Chief Privacy Officer has air cover…and so that I can ask others to do the same with a clear conscience.

During a crisis.  I may interact with Privacy infrequently, but oftentimes when I do, it’s because something has gone wrong, or we’re worried about something going wrong.  That’s ok!  As long as you can be there to support your Chief Privacy Officer on an emergency response basis and practice some level of servant leadership in a crisis (“how can I help here…who do you need me to call?”), you’re doing your best work in this department.

It’s important to have a regular cadence and a strong relationship with the Chief Privacy Officer because when a crisis hits you don’t want to miss any steps. While most of the time things run smoothly in the Privacy domain, the few times when things spin out of control those are the exact moments when you need to hit the ground running, trust your Chief Privacy Officer, and help get everything sorted out.

(You can find this post on the Bolster Blog here)

The last couple weeks, I’ve written about tools in the CEO toolbelt that I learned with my coach Marc years ago in a workshop called Action/Design — Inquiry vs. Advocacy, and The Ladder of Inference. The final post in this series is about Learning Loops (or Double Loop Learning if you prefer), popularized by Chris Argyris a couple decades ago.

Here’s the graphic on it:

What’s the tool in the CEO toolbelt here? It’s that every time you’re analyzing a result, you need to analyze it on two levels. Level 1 is the more obvious learning — “What happened…and what do I do next time to produce the same/a different result?” Level 2 is the less obvious learning — “Why did that result happen, and how do I need to think differently about the problem in the future?”

Think about how to apply this to a business result. You put a new pricing plan in place. Clients don’t bite. Loop 1 just gets you something like “ok, let’s try a different pricing plan.” But Loop 2 gets you “how did we come up with the pricing plan that failed in the first place…and how do we generate the next one so we don’t fail?”

Or think of how to apply this to a difficult conversation. You and your VP Eng on why a critical engineer left your organization abruptly. Your VP Eng is blaming Product for poor management of the agile process and product design; you believe it’s an issue of engineering team burnout. You can just go back and forth Advocating your points of view and maybe even Inquiring as to why those points of view exist, and even the powerful Ladder of Inference may not be able to help unless you have a great exit interview. Double Loop Learning is an offramp from that kind of conversation in that you can add that Level 2 questioning to the mix. It’s not about “what do we tweak so another engineer doesn’t leave tomorrow.” It’s “is there a systemic problem here with the way we produce product (or even broader – with our product/market fit) that doesn’t encourage the best team members to stay here?”

The best CEOs are the ones who are constantly listening, learning, adjusting, and executing. Hopefully these three principles — Learning Loops, Inquiry vs. Advocacy, and The Ladder of Inference will all help you on your journey.

This is the third post in the series. The first one When to hire your first CPO is here and What does Great Look Like in a CPO is here).

Chief Privacy Officers who aren’t scaling well past the startup stage are the ones who typically have the following characteristics and you should look for some of these telltale signs.

First, if your Chief Privacy Officer looks at you sideways when you ask for a strategy or even a mitigation plan for a breach, then you might have a bigger problem than the fact that you don’t have a plan.  While we like to talk about things like Privacy by Design and using data protection as an offensive strategic weapon, the reality is that Chief Privacy Officers need to have actionable plans in place at all times for the areas where they judge your company to be the most vulnerable.  If you ask to see the plan or get briefed on it and you get back a blank stare, you know you have a reactive person on your hands for what needs to be a thoughtful proactive role.

Second, you might have a Chief Privacy Officer who is not scaling if they would rather lecture you on GDPR than talk about why your data protection plan will win business.  Privacy people can be geeky, legally-oriented, policy-focused and very technical.  All that is well and good but there is so much more that a great Privacy Officer can do. For example, if your Chief Privacy Officer can’t engage in strategy with you and other executives and understand the levers of your business and how their role can help further them, you may as well use an outside law firm instead of taking up a valuable seat at the table internally.

The Privacy team can be small and somewhat insulated from the business, but your Chief Privacy Officer needs to be able to engage the entire company, they need to be thinking strategically about the business, and they need to have short- and long-term plans in place for contingencies and forseeable roadblocks. If they can’t bring these skills to the table at startup scale, how can they bring them to the table when things really take off?

(You can find this post on the Bolster Blog here)