How to Manage the Fallout of a CTO Crisis for Better Outcomes

Founders and C-Suite warriors, do you have a CTO disaster on your hands?

You vetted your CTO.  Perhaps you could have done the job yourself but you are busy running your business.  You were so convinced that the talent you hired was doing their job because of the appearance of a good track record, some serious smooth talking, cool PowerPoint slides, a nice wireframe, a workable strawman for a pilot, or reasonable excuses for missed deadlines, etc.

But the fact is that the person you hired did not do the job you paid stacks of cash for and told your biggest clients would be done.  You did not expect somebody to mislead you when checking in regularly about progress and anticipated deadlines.

But when it was time to deliver the product, you had ice water thrown in your face right before your *ss was set on fire because you had to go tell your customers YOU COULD NOT DELIVER. 😭

You are not alone.

ANATOMY OF A DISASTER

How does this sort of thing happen?  How often?  You try to hire good people that can be held accountable but sometimes good problem solvers cannot follow deadlines, cannot manage others, cannot admit when they are in over their heads, or are seriously good bluffers.  Sometimes it is a communication disconnect that is identified too late which prompts silence, a cover up, or someone to ghost you entirely.  👻

Sometimes, it is you.

Too often, people await very large technical deliverables with insufficient check ins or without the right kind of progress tracking.

The sooner you understand what led you to the brink of disaster, the sooner you can fix the situation.

The proliferation of innovative technologies across all sectors and functions means that someone in your organization, regardless of how low tech, needs to be on top of AI applications that your competitors are mastering to better serve customers.  Understand and leverage new technology to your benefit or you might become roadkill.

YOU CAN STILL SALVAGE THE SITUATION

Is it over for you in an existential CTO crisis?  Not necessarily.  It is time to regroup.  You need to offer something to your clients to get them to hang in there until you can actually get somebody to do the job your CTO was supposed to do.

Expect to lose some customers for sure.  But expect to keep some as well who believe that you are capable of meeting their needs.  I have advised many founders whose house caught fire because of CTO disasters.  Yet they were able to manage the situation and cross the chasm that can take down companies, talented people, and promising innovative technologies.

HOW TO MANAGE THE CRISIS

Unpack the problem.  Identify what has been done so far, what needs to get done, and triage.  Must haves should be divided into easy vs hard fixes.  Nice to haves need to be postponed.

Identify available resources.  Can you get the work done with the technical people you already have?  What can you do yourself?  What might you need to outsource, even if temporarily?

Identify and gain consensus on the process.  What needs to be done immediately?  What is feasible?  How can the process be optimized with the fewest steps and resources?

Communicate the process.  Customers, marketing, and technical staff must be informed of where product development stands, the setbacks, anticipated fixes, likely timing, and incentives to keep working together intentionally and productively.

Agree upon new objectives, deliverables, and timing.  Focus on shorter achievable timelines.  Do whatever it takes to make your customers and technical talent feel heard, appreciated, and able to rely on you as needed.

Stay the course. Pivot as a strategy, not a reaction.  You cannot get anything done if you are changing the requirements too frequently.

HOW TO AVOID DISASTER:  10 TIPS FOR BETTER OUTCOMES.

Tip One. Know Your Talent. A coder or technical expert does not equal a CTO.  Founders of early stage companies with lean resources, and the urge to show a complete team, will often put people in this strategic and administratively demanding role who are not the right fit.

Understand the difference between an individual contributor who does well on their own with direction versus a manager of technical talent, resources, and product development timelines with initiative.  It is okay not to have a CTO if you are not ready for one.   But someone needs to be on top of the product development iterations and pivots.  Yes, it needs to be you.

You can develop a technical talent hire into a CTO role by assigning that person roles of incremental management responsibility with promotional titles such as technical lead, manager, or director prior to CTO.

When it comes to due diligence, an investor or acquirer notices if the CTO is someone new.  Less significant to investors or potential acquirers is if a lower level tech manager is swapped out.

Tip Two. All Must Listen to Customers. Everyone must be client facing.  Really.  Always.  Technical people become more motivated and productive when part of the client solution team.

Regular conversations about what the customer needs, how, when, and why can spark a productive iterative product development cycle.  Regular feedback from current and/or potential customers on specific features in a variety of development stages (from low fidelity mock ups to partially built prototypes) will drive progress and minimize misalignment of deliverables.

The reality is that people observing the same thing will internalize different things.  Talking about what everyone thinks they heard, learned, and will do next is invaluable and will free up your time to run your business.

Tip Three. Build Lean and Create a Flexible Roadmap. Don’t overbuild.  Start with simple features to engage customers even if you really want to deliver more.

Be clear about objectives, deliverables, and create a protocol for pivots and blow ups.  Articulate and agree upon what success might look like and set metrics to judge success.

Tip Four. Measure Incremental Progress.  Set mini-milestones, small progress deliverables, and check ins to ensure a regular workflow.  Waiting until a big deadline for a deliverable can be a recipe for missed expectations.

Technical systems are designed in components.  Each component should have snackable size deliverables and time-bound iteration plans.  For example, you may have an initial design component such as a database, then an interface with other internal components, next an interface for customers, and auto-feeds.  Collaborate and evaluate in iterative steps.

Tip Five. Face to Face! In your face management helps.  You need to make sure that what has agreed to get done is getting done and that you are there to help when the technical team is unclear about any aspect of the task.

Get outside help if you need it to logic check what everyone is doing at critical junctures.

Tip Six. Allow Failure.  Give second chances but don’t be a pushover.  Brilliant people sometimes just need more time to get up to speed.  Give your technical people time to learn, be creative, and iterate.  Your CTO needs to be allowed to make mistakes but must also be held accountable to communicate them to you and fix them in a timely basis.  Build in some time for this and you may see much better results in a reasonable amount of time.

Tip Seven. Align Incentives.  Match incentives to milestones which should also include management, reporting, and problem solving achievements in addition to product development goals.  Have equity earned month to month and linked to milestones versus granted outright.

Tip Eight. Encourage Upward Feedback.  This is sometimes hard because you want to be respected, heard, and not walked over when you are just trying to figure out the best way to run your company with never enough time.  Allow your technical staff to give you constructive feedback as it relates to choosing, evaluating, and communicating deliverables and progress. Creative tension can be a good thing as long as it is productive.

Tip Nine. Understand Your CTO’s Point of View.  It is in the nature of builders of technical solutions to underestimate the complexity of deliverables.  It takes time to build systems, especially uniquely innovative ones.  It is very difficult to get anything done if directions are changed every few weeks.

Most CTOs do want to please you and will agree to overly complex and constantly changing requirements as the nature of their work.  Many will not want to appear incapable of working independently and managing their resources as requested.  They may not want to bug you until their work is complete according to your requirements.  Allow your CTO to be heard and assisted by you without asking.

Tip Ten. Don’t be the Problem.  Take responsibility for how you communicate, the changes you request, the prioritization, and the agreed upon deliverables.  Repeat, pivot as a strategy not as a reaction. Be collaborative, a good listener, and nurturing.  It is okay to make mistakes.  Own them and fix them.

And yes, sometimes it is totally not you.  Be alert, involved, and prepared to make the tough changes necessary to push forward.

Chin up!  Go do this thing!  Reach out if you need someone to listen to you and figure stuff out.

About the Author

Joy Fairbanks is an experienced institutional investor, builder, innovation advisor, and educator. She is Managing Principal at Fairbanks Venture Advisors, an Operating and Investment Partner at Portola Valley Partners, and a Partner at Silicon Valley Women Founders Fund.

Joy has served as a faculty member at Columbia Business School running the impact venture incubator and helped launch the Long Beach Accelerator, a public private partnership. She has worked with a wide range of accelerators including Techstars, Blackstone, Village Capital, Venture Out, Columbia Venture Community 2.8 Womens Accelerator 💙🦁, LBAN/Latino Business Action Network, Stanford's Hacking for Recovery, Cal Hacks, and NYU's New Media Lab.

Joy advises over a hundred tech startup founders per year across sectors and geographies on product development, market assessment/customer acquisition strategy, partnerships/pilots, financial forecasting, funding, M&A, and exits. She is a requested speaker on these topics and writes about startup success at FairbanksVentureAdvisors.com.