Name: Darren Platt
Time with company: 5.5 years.
Education: Bachelor of Science in Management and Information Systems, Rutgers University
Company headquarters: Boulder, Colorado
Countries of operation: U.S., U.K.
Number of employees total: 80
Number of employees the CTO oversees: 35
About the company: Symplified provides identity and access management across cloud, Web and mobile apps used by employees, partners and customers. Symplified protects more than 4 million identities for customers in the health care, financial services, manufacturing and telecommunications industries.
1. Where did you start your career and what experiences led you to the job you have today?
I think it’s worth mentioning that I started my career in high school. I started programming then. I was working on an application for a company that did direct mailing. I helped convert a program that ran on the mainframe so that it could run on the original Macintosh. It was a small company and it was really exciting to do what I had been doing for fun and get paid for it.
The first job that really shaped my career was the first one out of college. I worked for a large telco. My first job was as an interbilling systems test coordinator, which meant that after QA had run its cycle and found bugs with the billing systems at this telco it was my job to go around to all of these people and say, “You need to fix this bug.” What I learned about were the inefficiencies that could happen in a large enterprise and that made me want to work in a different way.
I was really frustrated. There was no accountability and nobody would be cooperative. I quickly realized it was not a good situation or a good company to work for.
From there, I went to a consulting company in Manhattan called American Management Systems and then I went and started doing startups and this is my third startup since then.
Different people have different styles and you should work where your style fits, and mine is definitely not in a big monolithic company.
2. Who was an influential boss for you and what lessons did they teach you about management and leadership?
Bill Wood was influential in a lot of ways. I’d say the big lesson I learned from him was about how career transitions work for technical people and how it affects their motivations and most specifically how as people move from a hands-on technical position to a more managerial position, their natural desire to create something can make them do things that aren’t necessarily in their own best interest.
What I mean by that is that most engineers are creative people, certainly the best, highest-performing engineers I meet get a lot of satisfaction from creating and building things. Outside of engineering, they’re doing art or restoring trucks or building things. So when you get someone like that who gets satisfaction out of building and developing code and then you make them managers, they lose that immediate satisfaction they get from building working code. That can lead first-time managers to go back to spending time coding so they can satisfy their inherent urge to create something, at times when they should be focusing on leading others.
That piece of learning was great and really helped me be a better manager and help people through that transition.
3. What are the biggest challenges facing CTOs today?
I’m sure there are different challenges depending on what kind of company you’re a CTO of. I’m the CTO of a late-stage technical startup, so within that context my biggest challenge is striking the balance between spending time on tactical issues and strategic issues and initiatives. Very often, I’m pulled into detailed design meetings and helping to explain how our company’s offerings add value and solve challenges around specific customer architectures and requirements. That kind of work is a very important part of my role because it helps me stay aware of the current challenges and opportunities in the market.
I also need to spend time on more strategic things such as planning the features that are coming up in future releases and researching and working on the open standards that our products implement. Each of these types of activities inform the other — for example having direct interaction with customers enables me to bring better data to our strategic planning meetings. So balancing those two types of activities is a challenge.
4. What is a good day at work like for you?
This is what we were talking about earlier — that as a manager you have to find other places to get gratification. For me, one of the best things that happens is when we promote someone or give them some other form of recognition. I get great satisfaction having helped create an environment where someone has developed their skills and/or made progress in their career.
Another indication of a good day is one where I get to work with a team in coming up with a unique or elegant solution to a technical problem. I think a lot of people think the CTO gets to do a lot of that, but it’s really not always so. So it is really enjoyable when it happens. Along those lines I also really enjoy product design from the standpoint of figuring out which set of features will provide the most value to customers.
As our company has grown, my role has evolved and now a big part of what I do is help explain to other companies where our product fits into a larger enterprise architecture. It’s very satisfying for me when I can expand the way someone is looking at a challenge and help them see new ways of solving it. It’s great to see the relief in people’s eyes when they realize things aren’t as bad as they think they are.
5. How would you characterize your management style?
Empowering. By that I mean involving employees and really getting their buy-in for the work they plan to do and the commitments they make. A big part of that is involving them in the process of determining the work they will commit to doing and the timeframe they will do it in. The Agile development methodology accommodates this negotiation very well. As a manager, I need to be making sure employees have every opportunity to be successful and consider it part of my role to remove any roadblocks that may get in their way.
The other side of empowerment is holding people responsible for the commitments they make. Providing this feedback is critical in building a high-performing team.
I’d say there are two more aspects worth mentioning. I believe communication is critical to an organization of any size and needs to be considered as part of the hiring process and then actively encouraged among employees. Everyone needs to be working from the same “playbook” so that we aren’t working at cross-purposes or duplicating effort. Another key part of communication is around expectation setting. In an enterprise where we rely on each other to the extent that we do, everyone needs to know what they can expect from each other. Priorities can change quite often for an enterprise and this often requires people to change what they are working on. It is critical at these points that everyone know what they can depend on from others.
For example, if one of my reports is going to miss a deadline for getting a report in, I want to know about that really early. I want to make sure that people can communicate where they are with things without fear.
Also, I’m results-oriented. I’m not counting how many hours people are in the office. I don’t care about that. What I care about is that they’re challenging themselves with the commitments they make, take those commitments seriously, and that they do quality work.
6. What strengths and qualities do you look for in job candidates?
The one that is implied [in what I’ve said] is people who take their commitments seriously and are responsible. I believe that if you give that kind of person the ability to make their own commitments, they’re very likely to meet them. They’ll be very motivated because the commitments they’ve made are not ones you’ve made for them.
I think independence and the ability to work on their own and figure things out on their own are also important. When confronted with a challenge, some people’s first inclination is to schedule a meeting or find someone to explain it to them. In the technical space, people always need to leverage new approaches and those who can do that on their own are very valuable. In a startup, we need people who can wear a lot of hats and people who don’t need a pre-defined corporate procedure for each thing they need to do.
They’ve got to be intelligent, obviously. But not necessarily super-skilled in the area we’re working in, because if they have those other skills I described, they’ll come up to speed.
We’ll also have a prima-donna conversation before somebody starts. We’re not going to have prima donnas, and I’ll tell candidates that directly. I’ll also ask questions to help me understand how well they work well in teams.
7. What are some of your favorite interview questions or techniques to elicit information to determine whether a candidate will be successful at your company? What sort of answers send up red flags for you and make you think a job candidate wouldn’t be a good fit?
The main technique I use is to get people talking about the projects that they’ve worked on and ask them a lot of questions and then drill into one of their projects where I may have some technical expertise in that area, and then I ask them some questions and try to figure out if they’re going to B.S. and pretend to know things they don’t know. If I can’t find a way to get someone to say “I don’t know,” that’s a red flag for me.
As for questions, the first one I ask is what they think the differences are between working at a big company or a small company or a startup. Depending on if they’ve worked for a startup or not, I’m looking for different kinds of answers. I want to hear, “I get to wear a lot of hats and do a lot of things and influence a lot of things.” A bad answer would be “I get to bring my dog to work” or “I don’t know the difference.”
I also ask people how they organize their workday, if they have a system to stay organized or if they’re just winging it. I don’t really care what the system is (as long as it makes sense), I just want to know that they’ve got one.
I ask them how they got into software development in the first place. Passion for this work is important and how they got into this career can help me gauge that.
The last question I ask is how they like to handle disagreements about technical points of view. I might ask them if they’ve ever had a heated discussion around a technical issue. This will help me to understand if they’re a prima donna.
8. What is it about your current job, at this particular company, that sets it apart from other chief technology positions?
I would say it’s the engineering team I work with. They have all those qualities I mentioned. They’re pragmatic and open-minded and obviously super intelligent and always coming up with great ideas. It’s exciting to work with that team.
9. What do you do to unwind from a hectic day?
I like to go home and spend time with my family and take my kids out on hikes. I think that’s the best one for me, is spending time with my kids. I also like mountain biking.
10. If you weren’t doing this job, what would you be doing?
I think I’d be teaching computer technology to children. What I’d really try to teach kids to do is how to create information technology rather than just how to use it. They don’t have to go off and be developers, but understanding how software is created will be a very valuable asset to anyone using computers.
And I’d really like to see us have better open-source software for education and I’d really like to get involved in that.