CIO Spotlight: Dustin Bolander, Clear Guidance Partners
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CIO Spotlight: Dustin Bolander, Clear Guidance Partners

Name: Dustin Bolander

Company: Clear Guidance Partners

Job title: CIO

Date started current role: Jan 2019

Location: Austin TX

Dustin Bolander worked his way through a variety of corporate jobs in his 20s before realizing his love for smaller businesse. He made the move into consulting, and now owns a business that provides fractional/outsourced CIO services (as well as general IT) to small and midsized law firms.


What was your first job? Our family had a dog training and boarding business, so when I was 11 I would go in with my dad on the weekends and scrub the dog kennels out.

Did you always want to work in IT? I did not, for the longest time I was wanting to finish my engineering degree and was working IT to pay for school. At about 28 I realized that IT was officially my career.

What was your education? Do you hold any certifications? What are they? I have a computer science degree, and several Microsoft certifications including a 2008 MCSE. The last few years I have not been spending as much time on certifications since I am not in the trenches as much.

Explain your career path. Did you take any detours? If so, discuss. I think I had a pretty traditional IT path, I started off working night shift helpdesk in college and worked my way up from there.

What business or technology initiatives will be most significant in driving IT investments in your organisation in the coming year? Client audits are a big deal in law firms, and getting more common. The clients are driving compliance requirements that most smaller firms cannot currently meet.

What are the CEO's top priorities for you in the coming year? How do you plan to support the business with IT? The executive committee, managing partner, or technology committee/partner is my "CEO" at a firm. In addition to client audits, a lot of firms are coming to terms with technical debt - having technology that was frozen in time 5 years ago. So lots of bringing in up to date and new technology, which includes updating workflows (lots of documents at a law firm!) and extensive user testing and training.

Does the conventional CIO role include responsibilities it should not hold? Should the role have additional responsibilities it does not currently include? Many firms would be well served to have a technology support role outside of the traditional helpdesk & administration. There is a large amount of work involving eDiscovery, where we are having to collect and handle data, often involving millions of documents in different formats (PDFs, emails, Office, and even a lot of TIFFs).

Are you leading a digital transformation? If so, does it emphasise customer experience and revenue growth or operational efficiency? If both, how do you balance the two?

Describe the maturity of your digital business. For example, do you have KPIs to quantify the value of IT? We track basics such as ticket response and resolution times, uptime, etc. The biggest thing is the satisfaction of staff and attorneys. If they view technology as an asset and not a hindrance, we are doing a good job.

What does good culture fit look like in your organisation? How do you cultivate it? Internally we embrace people who can speak up and make decisions quickly. Day to day, law firms move very quickly so there is not always time to sit back and think about it. Attorneys are experts in their field, and usually expect that from whoever they are working with, so you need to be quick on your feet, and when you do not know the answer, know who does. This type of culture tends to be self-reinforcing (as does the opposite culture of not speaking up…)

What roles or skills are you finding (or anticipate to be) the most difficult to fill? A lot of the work we do is in the blended area of IT and more general business - compliance, reporting, document management, etc. It is not always easy to find people who can both sit in front of the executive committee and have the engineering ability to deploy a new server. Since we're a small company, we still rely heavily on those rock star generalists.

What's the best career advice you ever received? Don't defend an indefensible position. It is ok to be wrong about something or to make a mistake, when you double down or dig in, that is when you get into trouble. I've seen a lot of people, especially executives, shoot themselves in the foot this way.

Do you have a succession plan? If so, discuss the importance of and challenges with training up high-performing staff. I do. He actually started off answering phones, but was quickly identified as a high performer, and was volunteering for every opportunity he could. Give people the opportunity to get involved and prove themselves, and the high performers quickly prove themselves. Projects are a great opportunity to do this, look for the ones who take any chance to work on a project, even if it is something basic like helping to rack servers. The motivation to learn and be in the thick of it is a great sign of their potential.

What advice would you give to aspiring IT leaders? Learn the ins and outs of the business and/or industry you are in. As you are working with more executives this kind of knowledge is noticed and appreciated. People are saying the cloud will kill traditional IT jobs, my opinion is we'll all just shift more towards the business side.

What has been your greatest career achievement? Building a team that can function without me. You have heard the stories of the executive saying, "The CEO knows best because I am the CEO". That is not me - I love being able to sit back silently and let the rest of the team run a meeting, project or even the whole company. If you're having to do the majority of driving and leading on your team, that is not leadership. You should feel like you're functioning on a peer level most days, and your job is to remove obstacles and course correct when necessary.

Looking back with 20:20 hindsight, what would you have done differently? I worked under poor leadership for long periods of time and just accepted that is how it was, not realising that sometimes the grass can be greener. Everyone makes and is entitled to bad decisions (heck, I have made a lot of them). If you're coming in every day and cleaning up poor decisions by higher ups, or management's ethics continue to be poor, that is when you need to think hard about making a change. Those are not fixable things.

What are you reading now? I read The Economist every night before bed. I am also working my way back through Traction (by Gino Wickman) as well.

Most people don't know that I… am an introvert, even though I spend all day in client meetings, working with people non-stop.

In my spare time, I like to…work on my vehicles. I am a bit of a hoarder, we have a few BMWs, an old Jeep Grand Wagoneer, and some motorcycles. None of them are that nice though, if I have $10,000 I'd rather have a few different cars than a single nice one.

Ask me to do anything but… survive without my Outlook calendar. Even my wife sends me meeting requests for things.

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