Category

Leadership

When to Hire Your First Chief People Officer

(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…

Formula for Strategic Leadership

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…

How I engage with the Chief Privacy Officer

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…

Learning Loops

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…

Signs your Chief Privacy Officer isn’t Scaling

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 Ladder of Inference

Last week, I wrote about Inquiry vs. Advocacy, an important principle I learned early in life and then explored more deeply in an Action/Design workshop my coach Marc took our whole leadership team through years ago. This week, I’ll continue to riff on the theme of communications tools in the CEO toolbelt by talking about The Ladder of Inference (detailed article here). This is a great graphic from the article: Any time you’re struggling with opinions vs. opinions or people are jumping to conclusions based on a narrow set of evidence, this framework is your friend. The best way to start any tricky conversation with those characteristics is to start “at the bottom of the ladder,” meaning you start by…

What Does Great look Like in a Chief Privacy Officer?

(This is the second post in the series… the first one When to Hire your first Chief Privacy Officer is here) Most Chief Privacy Officers are fairly specialized, often coming from a legal or law enforcement background, but regardless of background I’ve found that ideal startup Chief Privacy Officers do three things particularly well. First, a great Chief Privacy Officer will work to create educated evangelists inside the company.  Our Privacy team at Return Path, under Dennis Dayman’s leadership, had a lot of experience and industry certifications, but that experience was not something only for regulators and other companies, or only bragging rights within their team. They also took the time to make sure others in the company, especially in…

Inquiry vs. Advocacy

My Grandpa Bill used to not want to talk about himself at dinner parties. When one of us asked him why one day, he said, “I already know what I have to say. What I don’t know, is what the other person has to say.” There are a few principles I learned years ago in a workshop that my coach Marc led for us called Action/Design. I’m going to try writing a few posts about them, and you can find some articles on them here. Inquiry vs. Advocacy is simple. Understand the balance of when you ask and listen vs. when you speak in a given conversation. Both are important tools in the CEO tool belt. My rule of thumb…

When to Hire a Chief Privacy Officer

(Post 1 of 4 in the series of Scaling CPO’s)  Most startups don’t have a Chief Privacy Officer and just rely on outside advice from external counsel or a privacy consultant. In Startup CXO our Chief Privacy Officer from Return Path, Dennis Dayman, strongly advocates for privacy to be baked into a startup at the very beginning. Some startups probably don’t have any help in this area at all but given the importance of privacy and security issues today that’s a mistake. If your startup doesn’t start life with a Chief Privacy Officer you’ll have to heed some warning signs and here are some I’ve picked up over the years. First, you’ll know it’s time to hire a Chief Privacy…

Bring People Along for The Ride, Part II of II

Last week, I wrote about Bringing People Along for The Ride by involving people in the process of ideating and creating change in your organization. That’s the most important thing you can do to make it easy for people to handle change. But what about the people you don’t or can’t bring along for the ride in that way? If you organization has more than 10 people in it, there will inevitably be people where you’re IMPOSING CHANGE ON THEM. And honestly, even people who are involved in designing change still have to live through its impact. Today’s post is about managing the actual impact. The best thing you can do as a leader in helping your organization navigate change…

Bring People Along for The Ride, Part I of II

One of the CEOs I mentor asked me the other day asked me this question: I need to start making my organization think differently – more like a startup that needs to scale and less like a project. People need to start doing more specific jobs and not swarm all over everything. How do I get people to “get” this without freaking out? Every CEO faces dilemmas like this all the time. One of my management mantras over the years has been, “You have to bring people along for the ride.” Fundamentally, that means two things. I’ll write about one of them here today and save the other for next week. First, bringing people along for the ride means you…