Where should a CEO begin with digital strategy?
Begin by deciding what is worth doing for your business, before you pick a single tactic. Most CEOs get handed a long list of things they should be doing online. For a small or mid-sized company, most of that list does not apply. The first job is sorting what matters from what doesn’t.
A lot of the CEOs I work with started in the same place. They knew digital mattered. They could see competitors doing things online. What they couldn’t tell was what was worth doing, or what was even possible. That isn’t a lack of intelligence. It’s what happens when nobody senior owns the digital picture.
Why does it feel so hard to know where to start?
Because everyone giving advice is selling a piece of it. The web developer says start with the website. The agency says start with ads or social. The software vendor says start with their tool. Each answer is reasonable from where they sit, and none of them is looking at the whole business.
So the CEO ends up with a pile of good-sounding options and no way to rank them. Picking one usually means picking whichever was pitched most recently.
What questions should come first?
Before any tactic, I start with three questions.
Who are your buyers, and how do they decide?
Not a persona document. A plain answer. Who signs off, who influences them, and what makes them trust a company like yours. For many B2B firms the honest answer is referrals and reputation, and that changes what digital needs to do.
What do they need to see when they look you up?
Almost every buyer checks you out online before they reach out, even when someone referred them. Your website and the rest of your presence need to confirm what they heard. If they don’t, you lose people you never knew were looking.
What one change would make the biggest difference right now?
Not five things. One, maybe two. A company your size can take on one or two initiatives and do them well. Past that, everything slows down and nothing gets finished.
What should you avoid at the start?
Avoid starting with a tool, a redesign, or a new channel before you’ve answered those questions. A new website built on an unclear message just looks better while saying the same unclear thing. A new social channel with no reason behind it becomes one more thing to keep feeding.
Also avoid the long plan. A thick strategy document with twenty recommendations tends to sit untouched. A short list you can act on beats a complete list you can’t.
Who should be making these decisions?
Someone senior who is looking at the whole business, not one piece of it. In a large company that’s a Chief Digital Officer. In a small or mid-sized company it’s usually nobody, and the decisions default to whoever is loudest. That gap is the real reason it’s hard to know where to begin.
Frequently Asked Questions
What is the first step in a digital strategy for a small business?
Decide what is worth doing before choosing any tactic. Start with who your buyers are, what they need to see when they look you up, and the one or two changes that would make the biggest difference.
Should I start with a new website?
Not automatically. If the message is unclear, a new site will look better without working better. Get the message right first, then decide whether the site needs to change.
How many digital initiatives should a mid-sized company run at once?
One or two. More than that and attention splits, work stalls, and little gets finished.
Who should own digital strategy at a company without a digital executive?
One senior person who can see the whole business and decide what is worth doing. Without that, decisions tend to follow whoever pitched last.
Not sure where to begin?
Send me a note and tell me what’s going on. I’ll tell you what I would look at first.


