Expert Insights: 20 Tech Leaders Share Lessons From Difficult Projects

As a tech leader, it’s undoubtedly satisfying to reflect on the times when you and your team “knocked it out of the park” with a project. However, experienced leaders know that they and their teams often learn the most from initiatives that don’t go as planned—or even fail altogether. The members of Forbes Technology Council have collectively overseen hundreds of tech projects and have experienced their share of both glowing successes and disappointments.

Below, 20 of them share lasting lessons they have learned through projects that didn’t go well and how the knowledge they gained has influenced the way they have approached new initiatives ever since. 1. Don’t Scale Your Team Too Quickly Trying to scale up with more people too fast is a recipe for failure.

My most important lesson is that you often get more done with a smaller, more focused team. There’s less overhead and more direct communication, and coordination can be kept to a minimum. Adam Tornhill , CodeScene 2. Identify Unknowns Early On One of the most important lessons I’ve learned from seeing tech projects go wrong is to identify unknowns early on and tackle them at the beginning of the project.

Normally, people plan well for the things they know and are aware of; the things that derail projects are the unknowns. Spend time at the beginning identifying these potential obstacles. Bobbi Alexandrova , Loopio Forbes Technology Council is an invitation only community for world class CIOs, CTOs and technology executives.

Do I qualify? 3. Ensure You Have The Right People For The Project Having the right people on the team is so important. On a previous project, my team lacked the necessary skills, communication and technical expertise to deliver successfully. I now approach new projects by making sure I have the right people on the team first.

Ravi Kurani , Sutro 4. Don’t Try To Solve Everything Yourself The most common mistake a tech leader (even an experienced one) can make is to try to solve everything themselves instead of relying on their team. A small team that is just trying to catch up with you while you pour all your free time into a project will lag behind and will not be able to keep up with your progress.

And you will not be fulfilling your duties as a leader—you will simply become an obsessed individual contributor. Boris Lapouga , WorkHQ 5. Prioritize Expert Guidance An ounce of prevention is worth a pound of cure. After a challenging tech project, I learned the importance of consulting top talent early on.

Now, I prioritize expert guidance to preemptively tackle challenges and adopt best practices, leading to more efficient and successful project outcomes. Net Kohen , LinkMe 6. Make (And Regularly Review) A List Of What You’ve Learned Learning from failure is one thing; applying the knowledge gained is a completely different story.

Often, I’ve noticed things that should have been done better, but have I applied my learnings the next time? Doing so can be tough, as it often means going against your intuition, experience and the beaten path. But it’s important to make a list of your learnings and consciously review them when the next opportunity arises.

Pawel Rzeszucinski , Team Internet Group PLC 7. Outline The Project Scope And SMART Objectives A lack of clear, well defined project goals leads to ambiguity, misunderstandings and scope creep. This results in delays, wasted resources and a final product that doesn’t meet expectations. By establishing SMART (specific, measurable, achievable, realistic and timely) objectives, outlining the scope and aligning stakeholder expectations, leaders can ensure projects are better managed, resources are allocated effectively and potential issues are identified early on.

Shelli Brunswick , Space Foundation 8. Set Expectations Carefully Setting realistic expectations is important. Things always take twice as long and cost twice as much as expected. When we fail in any manner—and we do, and we will—we have to remember the expectations that we set to gain buy in in the first place.

Setting realistic expectations up front and discussing possible failures (and your plans to address them when they happen) are essential. Greg Coticchia , Sopheon 9. Build A Visual Product Blueprint A tech project starts with a set of requirements, and the biggest challenge for leaders is that those requirements are never completely accurate.

Whether you are following Agile practices or working in a normal software development life cycle mode, clarity around requirements drives successful delivery of the final product. The best way to prepare is to have an inception session early on and build out a visual product blueprint. This can help teams realize value quickly.

Shiboo Varughese , CirrusLabs.io 10. Survey, Survey, Survey The old saying “measure twice, cut once” applies so heavily to tech projects. I’ve learned over and over that if the survey, planning and pilots don’t go well, you need to do them over again. If the customer thinks the timing and costs are going to be problems, wait until they see what comes of a poorly executed rollout! Variables and variations are fatal to a tech project.

Tom Roberto , SG Network Services 11. Don’t Assume Perfection Make sure what you plan to release has great quality out of the gate, but don’t be arrogant and think that you have it all figured out from an end user perspective. User feedback will be invaluable in driving you to phase two of the project, where you really start to home in on a successful solution.

Remember, “perfection” is in the eye of the beholder. Lewie Dunsworth , Nuspire 12. Don’t Wait For Users To Highlight A Product’s Shortcomings Reviewing the development process and understanding why gaps occurred is as important as avoiding having your users become your de facto quality assurance team.

An organization must be proactive if a release doesn’t live up to expectations. It’s better to be up front and candid than wait for users to highlight shortcomings. In B2B environments, building a partnership versus a vendor customer relationship is key. Mark Heymann , Mark Heymann & Associates, LLC 13.

Don’t Lose Sight Of Legal Innovation Sometimes it’s not technical innovation that needs to happen for a product to become a success, but legal innovation. When I joined a security token startup in 2018, the main challenge we faced was financial regulation. Now that the regulatory tide has turned in many places around the world, real world assets are making a comeback.

Marlene Ronstedt , Play by Ear 14. Be Agile And Open To Change One important lesson I have learned is to identify problems early and be open to changing things up. During one challenging project, we didn’t discover certain issues early enough. Now, I concentrate on checking things frequently, listening to feedback and addressing mistakes as soon as possible.

It’s important to remain agile, nimble and adaptable and be quick to make changes to keep a project on track. Neelima Mangal , Spectrum North 15. Let Failing Initiatives Die One of my projects that didn’t go as planned involved a new hardware component. The work exceeded the budget and timeline, and the component became obsolete long before the project was delivered.

Now, the prototype is nothing more than a paperweight in one of our meeting rooms. It reminds us to let a failing initiative die if it needs to. Martin Taylor , Content Guru 16. Reinforce The Value And Impact Of Large Scale Projects Many large scale projects come with the executive team’s high expectations of the level of enhanced organizational capabilities they saw during the sales cycle.

However, a new system often impacts employees’ daily work, requiring more “clicks” and workarounds. It’s important to reinforce the value the business will gain from the change and how everyone impacted is helping with the value transformation. Lou Senko , Q2 17. Ensure Ownership Backs The Project When it comes to any new project, ownership has to be behind it.

It doesn’t matter how smart, effective or beneficial to the company the project is; if ownership ignores it, then management will too. Seth Wasserman , Menin Hospitality 18. Align With Customers On Key Factors Successfully delivering a tech project for a client is usually about trust, chemistry and expectations.

Achieving alignment on these factors with your customers at the beginning of each project is crucial for a successful collaboration. Edin Deljkic , Klika 19. Don’t Ignore The Importance Of Change Management Ignoring change management alienates users, leading to adoption issues. Combine that with a lack of executive support, and you’ll drain all momentum from teams.

Executive sponsorship is a must at the planning stage. Embed executive communication and training within the planning process. Mani Padisetti , Digital Armour 20. Prioritize Performance And Speed One important lesson I learned from one of my early Microsoft projects is the importance of prioritizing performance and speed—“slow software will never win.” I now prioritize performance testing and optimization in the early stages of development to avoid potential issues in the future.

Robert Mao , ArcBlock Inc ..