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What do founders want to "Ask a CTO"?

I've been a founder or CTO more than a half-dozen times, and always find myself working with talented non-technical co-founders or CEOs (well, mostly talented...can't win 'em all, right?) I love the collaborative process of helping non-technical founders understand the product development process, tech team building, and the fast-moving and mind-numbingly large world of technology itself.

My premise is that every founder these days has to deal with elements of a technical product build, whether it be a simple blog, or a complex API-powered multi-platform enterprise mobile application. And especially for entrepreneurs who didn't grow up in the latest in-vogue "everyone learns to code" society, they will make a lot fewer mis-steps in dealing with their development team if they are armed with knowledge and best-practices.

While I'm taking some time off after my last startup exit (won't be able to stay away for long, I'm sure...), I'm writing more about these topics at http://www.clearlytech.com/

My questions to this awesome group are:
  • If you a non-technical entrepreneur, what are your top 3 issues you wish you had a better handle on? What are the things you'd "Ask A CTO" if you had a trusted one sitting around over beers. Anything from "Why does everyone seem to hate PHP?" to "How can I keep my developers from always shooting down my product ideas?"
  • If you are a technical entrepreneur, what are your top things you WISH your non-technical partners understood better? What's the stuff that would make your life easier if they understood better?
Finally, where do you find good tips and tricks if you are looking to better understand modern tech and development practices? Lectures? Books? Podcasts? Google Searching? Entrepreneur Blogs? Let's share some resources so my post isn't quite so self-serving!

Looking forward to your insights.

23 Replies

Michael Barnathan
3
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Michael Barnathan Entrepreneur • Advisor
Co-Founder of The Mountaintop Program, Google Alum
Simply, I wish nontechnical people understood more about how technical people work. The importance of uninterrupted time, consistent priorities, and a predictable release schedule. I view these things as prerequisite knowledge to managing a technology company.
David Crooke
1
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David Crooke Entrepreneur
Serial entrepreneur and CTO
Count me in as an experienced CTO who's willing to advise too.
Alison Lewis
1
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Alison Lewis Entrepreneur • Advisor
CEO/Creative Director
That response is great. As a designer and CEO, I wish my technology team was more flexible about deadlines and changes, and better at managing their schedules. I went and hired a product manager to help with our communication issues.

Both my designers and technologists have a challenge of giving to many specifics. I would like them to understand CEOs and founders deal with various complex issues from many different areas at once, getting too detailed into one for very long can hurt the company and their ability to lead with perspectives from many angles.

Otherwise, I love my technical team. I've learned to set objectives with their input, then make some dates and walk away and put a manager between us to sponge up all the details and pass the critical path info to me. A seasoned team working technical can do this as well.

The only question I have is why do technicals come off as so pushy about money? I've encountered many times asking for raises and asking for shares before they're even finished with the current contract. I find the methods of approach and the demands very off putting, makes me see them as having a risk adverse. It's a start up, demanding more financial compensation in the middle of a project, needs to be done with consideration and tact.
Mona Sabet
0
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Mona Sabet Advisor
driving growth | leading tribes | making deals | advocating for diversity
Love both Alison and Michael's comments. perfect representation of the tension between technical and non-technical people.

Like Alison, I'm thinking I need a product manager to help manage communication and expectation setting between me (non-technical) and my awesome technical team. Haven't done it yet because not sure if that's the right path forward.
Michael Barnathan
0
0
Michael Barnathan Entrepreneur • Advisor
Co-Founder of The Mountaintop Program, Google Alum
It depends: is technology your company's core area? If so, it's important that everyone on the founding team (i.e. calling the shots) understands how to manage a technical project. Otherwise you're just transferring the responsibility of the technical/non technical interface from the CTO to the project manager, and will probably experience the same clashes.

Nontechnical founders don't need to know more than a superficial amount of technology - enough to communicate how the product works and have a rough idea of how long feature requests might take (to avoid impossible expectations). But knowing how to *lead* a technical team is vital for the CEO of a tech company. Anything else leads to a disconnect between the person calling the shots and the people who have to deliver on those calls.

On the subject of tech people demanding more equity midway, that sounds dishonest. For what it's worth, I have had entrepreneurs fail to make good on existing vesting promises, though, so it does run both ways. The primary difference might be that a tech person can do a lot of damage to a small company by leaving, which gives techies more leverage. Some people probably take advantage of that.
Tom Maiaroto
1
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Tom Maiaroto Entrepreneur • Advisor
Full Stack Consultant
I think there's often too great a divide between "tech" and "non-tech" and somehow we continue to drive an even bigger wedge between the two "sides." I think that's wrong. There is no "side." If we're talking about a technology startup, guess what? It's technical...And the business co-founder better be on board with that and the sales people better understand what they're selling.

No one expects the "non-tech" co-founder to code...But like Michael said here, insight to just a little bit of the tech process is important. Understanding how the tech works is also important.

I've seen a lot of non-tech people go out and sells clients on something that simply wasn't possible, didn't exist, or was just described all wrong. Did they lose the sale? No! Funny enough...They were good sales people, the client bought the damn thing and then the tech team had to deliver. This is a very common problem. Another common problem is then failing to deliver what was promised. Both preventable.

Likewise though, the technical stakeholders don't typically understand business goals that well. They may want 10 years to build the best program in the most 1337 language and hibernate in some cave. Unfortunately that's dangerous.

This is where we kinda get into your question about "Why does everyone seem to hate PHP?" ... That's a terrible circumstance that's going around the web. Not just PHP, all language "wars" and "haters."

The internet is the wild west. There's really not many rules and if you ever come across a "CTO" who tells you that they only need one language/tool and all others are terrible - then ditch them. IMMEDIATELY. I can't express has fast and how far you must run away from them. A CTO should not "hate" on any language (or database). Dislike? Not be familiar with? Sure...But you MUST be open to using whatever is at your disposal in order to meet your business and product goals. The job must get done and if you use the wrong tool for the job, it could cost you your business. Again, preventable.

The decision on your technology stack, of course, may not come from a CTO either. Want to be a Billy Bad Ass and use some "enterprise" solution because some company sold you on the license and told you there's a 99.99% SLA and it's the jam? Some investor with a ton of money told you "this is how we do things partner" ? Well, you may need to be prepared to budget for the development and time costs. Often using those "enterprise" solutions means you're working at a speeddisadvantage. There's far too many startups and noise on the internet to be slow here.

Some other quick food for thought. IF you can safely build a product faster by using a different language, driving down your development costs -- how much more of your company to you get to retain? If you need less funding to build? Just food for thought.

However, we often see people vying for these kind of solutions because we might have someone who's background has always been from a slow corporate machine perspective. Or you have an investor or business co-founder who has bought into the false sense of security that some languages or "enterprise" tools like to push off onto people. Your technical tools should never be sold on you. They must be the right tool for the job and sometimes that requires some research and digging.

Just remember, it's the wild west. It wouldbehoove all parties to understand how shoot a gun, ride a horse, and cook food. Otherwise you're eventually gonna starve out there.Metaphorically speaking of course =)
Will Koffel
0
0
Will Koffel Entrepreneur • Advisor
Co-Founder at Outlearn
Tom, totally agree with your answer. And my apologies if my question "drove a wedge" further into the divide. I'm specifically trying to help close the divide. I don't believe that building tech products is "magic", and it always saddens me when founders think it is. Or don't ask the right questions. Or let their tech teams walk all over them, thinking that's just the way it has to be.

If you poke around my site, you'll also see that I'm in violent agreement around the tools-and-process-agnostic approach to dev. I could care less what frameworks or languages are used, as long as they meet the needs of the project. After building my last business on a PHP-based API serving thousands of requests a second, I can safely say I have a love/hate relationship with PHP. :-)

Your wild-wild-west analogy is a good one (mind if I steal it?). I'm looking to get a sense here what the product/technology equivalents are to "shoot a gun", "ride a horse", "cook food". That's exactly what we should be empowering non-technical founders with to help everyone get along a little more easily.

Will Koffel
1
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Will Koffel Entrepreneur • Advisor
Co-Founder at Outlearn
Michael and Alison, your point about the different working styles and different processing of priorities, urgency, and deadlines is totally a classic one I see all the time, thanks for bringing it up.

I posted one of my favorite reminder graphs on the topic recently:
http://www.clearlytech.com/2013/12/15/working-makers/

Alison, developers asking for more in the middle isn't too common, I don't think. Sometimes, it's just the market conditions right now, correctly or hype-fully telling developers they are worth more than they are getting. But often it's a side-effect of them losing confidence in what's being built, so they get nervous and want to make a grab for a bigger piece of what they perceive as a smaller-pie. Have a discussion with them about why they don't think their current stake is going to have a huge impact for them. Ask them if they wouldn't rather hire more great people with that extra equity, so everyone's stake gets larger. Might help tease out why they are nervous and getting greedy.

Alison Lewis
0
0
Alison Lewis Entrepreneur • Advisor
CEO/Creative Director
Interesting Will. I'm about to put the line out for a CTO, a CTO in a fashion design company is going be interesting. I'm interested in how others will respond to your post as well. Alison
Tom Maiaroto
0
0
Tom Maiaroto Entrepreneur • Advisor
Full Stack Consultant
Will, I didn't mean to make you think your question was driving any wedges. I just mean I understand and it's a very common theme.

I think everyone is in a love hate relationship with PHP =) But yea I really don't know why people "hate" on PHP so much, given it powers most of the web. It's also a really good example of being able to have a sinking ship. You could be taking on water and sinking, but the band is still playing and the lights are still on. Not many languages can do that.

You're more than welcome to steal the wild west analogy. Just give me some credit if anyone asks haha.
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