Make the case: Why should CIOs become advisors?

2.2k views1 Upvote13 Comments

Former Chief Technology and People Officer in Software, 1,001 - 5,000 employees
When Forescout got acquired by private equity, and my role was going to change significantly, it became a great opportunity for me to rethink my career and make a real pivot. I thought I wanted to be a COO. But in the end, I realized, you know what? So what, I can chase the COO role, it's the same stuff. Same circus, different clowns. Same challenges, so why not think about just giving back in a different way? I had already started doing some board work and I realized, "Hey, maybe I could pivot to more of that and less of the day-to-day operating role (which I really do not miss), and really be in a more consultative advisory role.” So far it is super rewarding. A lot of people think hands-on operators like us are not going to be able to make that transition and let go, but I have found it's really not that hard. I recommend this to everybody. I get a lot out of it and I don't have the Sunday scaries like I used to.
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Partner in Software, 1,001 - 5,000 employees

Sunday scaries and same circus different clowns. I think there's some t-shirts that we're going to need to make.

Director of Information Security in Energy and Utilities, 5,001 - 10,000 employees

Same circus different clowns.  <- This really deserves a good T-Shirt liked Yousuf mentioned. I had a good laugh when I read that as it's all entirely too true.

Advisor | Investor | Former CIO in Services (non-Government), Self-employed
An outstanding friend of mine switched roles from CIO to advisor. Every time I saw him he would just be telling me about this role he took on and how much enjoyment he's having with the role to the point he was saying, "I'm not sure I'll actually go back to the CIO role." We accumulate scar tissue along the way and I think the reason why we accumulate it is because we'll be able to apply that and give back so that others may not have to endure as much pain and suffering. If we can actually share some insights, some guidance, and help others, personally I find there's a lot of satisfaction from that. 

The role that I took on comes with no staff and no budget. And it's incredibly liberating, quite honestly, just to be in a situation where you can focus on the customer and not worry about doing one-on-ones, reviews and stuff like that. I can just focus on something that I enjoy. One quote that I do like is Charlie Munger: “Show me the incentive and I'll show you the outcome.” If the right incentive is there, what will actually transpire is hopefully an enjoyable outcome. And so for me personally, the way the incentives are structured right now, I'm enjoying what I'm doing and I think I've got the best of both worlds. On one hand I'm advising, on the other hand at the startup, but also involved in a pretty substantial company that's having an impact.
CIO in Finance (non-banking), 51 - 200 employees
Working in VC, the really core opportunity for me is impact, and not only impact to the partnership and getting deals and all that stuff, but also impact on the companies that we invest in. That to me was the bit that flipped for me to realize, "Okay, this is something different than the average CIO would do." The other piece that is fun is obviously hearing founder stories going from zero to one. I could just listen to people's stories all day. “I found this problem and this is how I solved it.” I eat that up like popcorn. And then the other part is when the founders need to hire a new role, expanding them to introduce them to other networks that we have is also super cool. It's really rewarding. I see us all as shepherds and guides to either small companies, big companies, transformational companies. It's really cool. Someone's raising their hand for help and we're more than happy to put out your hand and help and share, "Let me tell you about my journey. You'll get there, trust me. It isn't all facilities. IT is good." It's really like, what makes you get up in the morning? What type of impact are you having? It's more than just your immediate sphere but that the influence is really wide range.
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Former Chief Technology and People Officer in Software, 1,001 - 5,000 employees

The one thing that I think that's allowed all of us to do what we're doing is the fact that we were in a CIO role. These opportunities wouldn't have come if we hadn't done some of that heavy lifting early on.

Partner in Software, 1,001 - 5,000 employees
I've actually wanted to be in venture for 20 plus years. I joined a startup during university. I was just fascinated that this company was two people a year ago and it was now 200 and venture capital had invested in the company. To see that human and engineering talent and pure grit come together to build something. I think that was something that enamored me. I wanted to do company building. I went through a variety of CIO and CSO positions where I helped scale companies. It's a really hard but character building experience, to scale the company from 20 to 150 people. But it was all done with the end goal of joining a VC firm in mind. 

My decision to move to venture was really coming out of a personal passion. I realized that life is very short, so you need to basically optimize for fulfillment versus accomplishment. Over time it got to the place where I didn't feel that CIO was something I was personally growing with. I just said, "Look, I'd rather try and do something where if I can coach and mentor teams or leaders or CEOs and founders, I think that's probably much more fulfilling work."  Last year I heard that people I knew well had passed away because of COVID or that I could not resume a normal life for a while. I had the realization that life is very short and you should basically go for the win and give it a fair shot. And so I optimized for a career change that gives me fulfillment.

My passion was to be able to help businesses get to the next level. In VC I tend to meet with hundreds of companies every single month or a couple of months. I can only invest in four or five per year, but with my operating experience of 20 years I’m able to give feedback to a startup and say, "There's a very good reason why an executive would never buy this product and let me tell you why." And they're like, "No one's ever told us that." When I do that, I feel like I've provided some degree of benefit or guidance to a startup founder even if I have not invested. And so for me, that transition was much more about personal fulfillment than it was about anything else and I haven't looked back.
Advisor | Investor | Former CIO in Services (non-Government), Self-employed
I’m a cloud therapist, is the way I like to describe it. There’s tons of portfolio companies that want to embrace cloud, but really don’t know where to start. I work with all kinds of CTOs and CIOs to try and unblock obstacles that they encounter along the way. It’s nice that I can apply my learnings to help others avoid some of the repeats.
CIO in Education, 1,001 - 5,000 employees
Good CIOs should be able to bridge business and technical acumen together in a way that should make sense to anyone, which makes them appropriate advisors.
Senior Director, Defense Programs in Software, 5,001 - 10,000 employees
Advisory is an interesting space. For top CIOs that worked on critical transformations, it’s therapeutic to take an advisory role and a solid way to have greater impact for more people. Many of us spend the most time as CIOs talking to other c-suite leaders, so it’s natural transition.

On the flip side, depending on the advisory role it can feel like helping people with the same set of problems repeatedly. Climbing deep on new challenges feeds our own creativity - and advisory can limit this.

I perform trusted advisory now. The impact I get to have is exciting. But there is always a part of me thinking about other roles to go deeper on individual opportunities. That might make me all that better of an advisor?
Director of IT in Finance (non-banking), Self-employed
CEO in Software, 11 - 50 employees
CIOs should become advisors for a number of reasons (assumption: you aren't saying they should forsake being a CIO, but rather that they should also be advisors): 

I'm asked to speak on industry topics an average of once a week? While the simple assumption by me is that I will share information and at the same time widen the audience for my company (by accident), I always learn something as I research my topic. 

Yes, I often do know the topic pretty well already, but I like to be sure I'm not making too many assumptions. 

Being an advisor gives you a direct opportunity to see what others are doing with their business and their technology investments. If you're doing the role of advisor correctly, you're likely to learn as much from each advising opportunity as the people being advised, learn from you.
Director of Information Security in Energy and Utilities, 5,001 - 10,000 employees
Personally speaking CIO's should be advisors due to the broad scope of their experiences. Rarely do you come across roles that interact that much with various stakeholders: board, customers, engineering, operations, sales. etc. All while operating and giving guidance to fairly significant operations as well. Ability to stay calm under pressure is something that all CIO's get sooner or later (after one too many operational issues), so if you can calmly digest the situation at end, reflect back on your experiences you can provide excellent advise to others to avoid either pitfalls that you had yourself or have heard about or think could happen. CIO's are fairly unique role and ability to advise is one of their greatest strengths (if underrated) so having an experienced CIO as your advisor is a great fit for any organization.

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