We are technology focused and senior leadership is revenue focused. We are tactical by nature while they are strategic. To work with senior leaders, we need to switch voices.
First, give them a lot of space to talk. Be direct with answers and then stop. Get good at 3-5 sentence answers. Let them jump back in. Let them finish their thoughts. Let them talk to each other without you interjecting. Wait for them to come back to you.
More importantly, listen. Think about what they are saying instead of what you are going to say. Respond to their thoughts and ask clarifying questions if you do not understand what they need from you. Keep detailed notes and do not make leadership repeat themselves.
Create intentional conversation starters or recommend questions for them to explore. Senior leaders are more engaged in presentations than other audiences. They will redirect you towards their needs if you create space for them.
Few decisions get made after a single meeting or during a meeting. Expect that. Follow up by email and ask if they have any questions. Be persistent but patient. Think about the different priorities they are balancing and respect their need for time.
If you try to dive straight into a prototype demo, you'll lose senior leaders. You sell them the value first. Once they agree on value, the prototype makes it real and easy to say yes to. Prepare hard number ranges for the project. From there, ask if they want to see the demo. That question will let you know if you sold them or lost them.
This is the blueprint for most conversations. Value first, technology presented in a non-technical way second. Make it real for them not confusing. Give them enough familiarity with the solution for them to be comfortable discussing it with other non-technical stakeholders.
The easiest way to lose leadership's trust is to overstate the impact of your project. Make sure the cost savings/revenue are provably attributable to the project. You may stray into another team’s value add. The team whose work you try to take credit for will burn you.
Realize they are going to give you credit for the project. However, publicly they are going to take credit for the project. You will sometimes get mentioned. That is the game. You make them look good and you advance as a result. However, the point is to make them look good because when they look good, the whole organization looks good. The benefits of them getting credit are broader than an individual or small team being in the spotlight.
Avoid early moonshot Machine Learning projects. The business needs time to grow capabilities and trust in the technology. Year 1 and 2 should establish a 6-8 week delivery cadence with 5X-10X returning projects. Celebrate success and talk about revenue or costs savings regularly. Establish a track record for results.
Also remember, you can save the business a lot of money by saying, "This is not a Data Science problem." Most business problems can be solved with ML but only the highest ROI projects should be solved using ML approaches. You build a lot of credibility by choosing the best use of your time. Be focused and selective.
Get comfortable using terms like Artificial Intelligence, RPA, BMI, IA, and Digital Transformation. That's what your business and customers call it. Using their terminology will make you a more successful communicator. Keep up with the buzzwords no matter how you feel about hype. Just get past it.
Machine Learning strategy requires everything on the product roadmap to connect with internal stakeholders' goals. The message? "We don't build anything until you understand the value it brings to your org." Be obsessive about it. Don’t fall in love with an idea because there are always 100 more right behind it. Let stakeholders guide you and use their support when talking with senior leadership.
Ask yourself if the results you are promising are interesting? Is that amount of revenue enough for them to get engaged? The higher you go, the more money it takes to get attention.