Drive has 700+ articles for digital transformation leaders written by StarCIO Digital Trailblazer, Isaac Sacolick. Learn more.

You have a big idea – maybe for a customer-facing application that will drive revenue, an analytics dashboard to help operations reduce quality issues, or a marketing campaign that may attract new prospects. Right now, it’s just an idea, but you want to invest a few hours per week researching and planning a business case. What should you do?

Develop Meaningful Relationships with Business Stakeholders

You have three options: (1) Do nothing – and maybe regret it later, (2) Plan the project on your own (i.e., a skunkworks project), or (3) find one or a few executives to partner with on the vision and planning.

I prefer and advise Digital Trailblazers to open door #3. I’d rather get a partner onboard, even though that often requires stepping out of your comfort zone. If you read or listen to my new book, Digital Trailblazer, you’ll see that taking on this challenge is critical, even though you probably would rather jump right into planning and implementing.

No relationship with a key business stakeholder?

Many of us, including me, are introverts. The idea of approaching someone you don’t know can be super intimidating. So, if you need to connect with an executive or key business stakeholder and don’t have a preexisting relationship with them, that can feel like an insurmountable barrier.

Some will give up without trying and go to door #2, but this is often a mistake. You might invest a lot of time researching and planning a dead-end program. And if you believe you have a unicorn idea, well, then you’re back to opening door #3 and needing stakeholders and sponsors. Why not get them involved from day one?

The real hurdle is approaching a business stakeholder, knowing that you don’t have all the background knowledge, business context, and a solidified idea.

So let me help you fix this in two steps: first, developing a new relationship with a business stakeholder and then transitioning it into a meaningful relationship.

12 steps to create a new relationship with a business stakeholder

I recorded my very simple, 12-step plan in episode 52 of the Driving Digital Standup that you can watch in under ten minutes. Watch it below, and I hope you’ll subscribe to the channel. Then, please scroll below it for three more steps on going from a new relationship to a meaningful one.

Transition from new to meaningful business relationship

In the video, I recommend going through the 12-step plan at least three times before conceptualizing the following ongoing practices. You’ll develop a solid relationship if you do these three activities consistently.

1. Prepare to give a lot before asking for anything in return

The best salespeople I know give, give some more, and continue giving. They don’t ask for much and often don’t have to because they prioritize building relationships with buyers and decision-makers that will most likely ask them for assistance.

At your business, you’re not selling in the same way as a vendor. You’ll likely have to ask for sponsorship, investment, and partnership, but if you play your cards right, it won’t feel like you’re asking. It will feel more like a discussion and an agreement to work on something together as a partner.

So, give continuously. Provide feedback, data, and insights. Share opinions.

2. Break bread whenever possible – travel together if it’s an option

Chapter 6 of Digital Trailblazer starts with my flight to India with Eleanor, an executive at my company. We were heading there to meet technology companies, but part of my objective was to forge a partnering relationship with her on several objectives. Today, Eleanor is a mentor and a good friend.

We started working together long before that trip to India, but our relationship truly developed through our regular breakfast meetings.

Breaking bread is a key step to developing a personal relationship.

3. Guide them on options and let them decide

Digital Trailblazers should consider themselves as innovation and transformation guides. Learn the customer value proposition and market needs. Understand opportunities and pain points. Recommend solutions.

But want a meaningful relationship with the business stakeholder or key decision maker? Give them options, and let them decide a course of action.

Are you ready for door #3? I would be glad to answer your questions.

Published on:

Leave a Reply


StarCIO

My company, StarCIO, provides leadership, learning, and advisory programs for companies looking to accelerate delivering business value from digital transformation. Contact me if you’d like to learn more about partnering opportunities.


Isaac Sacolick

Join us for a future session of Coffee with Digital Trailblazers, where we discuss topics for aspiring transformation leaders. If you enjoy my thought leadership, please sign up for the Driving Digital Newsletter and read all about my transformation stories in Digital Trailblazer.


Coffee with Digital Trailblazers hosted by Isaac Sacolick

Digital Trailblazers! Join us Fridays at 11am ET for a live audio discussion on digital transformation topics:  innovation, product management, agile, DevOps, data governance, and more!


Join the Community of StarCIO Digital Trailblazers

About Drive

Drive Agility, Innovation, Transformation

Drive is the blog for digital transformation leaders brought to you by StarCIO and Isaac Sacolick.

Agility, Innovation, and Transformation are the three primary digital transformation core competencies that every StarCIO Digital Trailblazer must champion in their organizations. Learn more About Drive.


About the StarCIO Digital Trailblazer Community

StarCIO Digital Trailblazer Community

Revolutionizing traditional learning, networking, and advising experiences.

Visit the community


About StarCIO

StarCIO

About Isaac Sacolick

Isaac Sacolick

Author, 1,000+ articles, keynote speaker, Chief StarCIO Digital Trailblazer. Full bio


Driving Digital Newsletter

Driving Digital Newsletter

StarCIO Guides

StarCIO Agile Planning Guides

Digital Trailblazer

Digital Trailblazer by Isaac Sacolick

Driving Digital

Driving Digital by Isaac Sacolick

Driving Digital Standup

Driving Digital Standup

Coffee with Digital Trailblazers

StarCIO Coffee With Digital Trailblazers

Recognition

InfoWorld 2025 Judge
InfoWorld Technology of the Year 2024 Judge
Thinkers360 Top 10 in IT Leadership
Thinkers360 Top Agile Thought Leader
Thinkers360 Top DevOps Leader
Thinkers360 Top in Digital Transfomation
Thinkers360 Top in Analytics
Thinkers360 Top in Product Management

Discover more from StarCIO Digital Trailblazer Community

Subscribe now to keep reading and get access to the full archive.

Continue reading