My 7-step goal setting system (free):

Every “guru” says business goals are important.

But no one actually tells you how to do them right. Nine times out of ten, goal setting makes things MORE CONFUSING, not less…

I call it the illusion of alignment.

Everyone thinks they’re rowing in the same direction, when they’re actually rowing to completely different islands. The drift gets bigger each month. By the end of the year company results suck. Regardless of individual performance.

How does this happen?

Lack of leadership discipline.

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Most leaders are “yes” people. They chase shiny objects, thinking each one holds the secret to greatness. They hate goals because commitment pins them down. Or, they set too many goals to create wiggle room, rendering them useless.

Operational excellence is the opposite. Focus and depth win markets. Not spray and pray.

My mantra:

“Win by going deeper than anyone’s willing.”

I pick my target customer and execute with maniacal focus. Everything I create must be 10x better than what exists. How? Obsessively go deep into the customer’s problems, where others aren’t willing to go.

Sound simple? Yet most people can’t do this. They chase the next exciting thing, before delivering meaningful value to their core customer. This creates a surface-level relationship you can exploit.

If you go deeper than anyone’s willing, and you’re already ahead. Your customers will love you, because its about them, not you.

I channel this attitude into goal setting. Where can the company double down on focus and depth?

That’s where real customer value lives.

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After 20 years of watching goals fail (including plenty of my own) I’ve identified exactly where things break down.

Before you say, “But what about [OKRs, Rocks, etc.]?!?!”, understand two things:

1. Any goal system breaks down with user error
2. Most existing goal systems have major flaws

These 7 essential rules fix those breaking points. Apply them to any framework you’re using, and your success rate will dramatically improve.

Want help rolling this out at your company? Create a free trial of Highland Academy, and search for the Masterclass on goal-setting. It also includes an instruction guide and template.

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Rule 1: Focus, then focus again

• Too many goals kill companies
• Maximum 3 company goals, period
• Goals aren’t a task list, they’re your top strategic priorities
• Keep each goal to just a couple words: “Successful launch into the enterprise”
• If everything is a priority, nothing is

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Rule 2: Always be measurable

• Define success with 3 or fewer metrics per goal
• Focus on outcomes (what success looks like), not tasks (how you’ll get there)
• “$1M+ in new ARR” beats “Update the enterprise sales deck”
• Company-level metrics should be purely outcome-based; team/individual level can mix outcomes and projects
• If you can’t measure it, you can’t improve it

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Rule 3: Challenging but realistic

• Goals should push you outside comfort zones without being delusional
• The “handshake”: Board signs off on company goals, CEO on team goals, managers on individual goals
• No sandbagging – mutual accountability prevents gaming the system
• 12-month timeframe keeps ambition grounded in reality
• Nothing kills momentum like impossible goals

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Rule 4: Never forget your ‘why’

• Every goal needs a 1-3 sentence explanation of strategic rationale
• Without context, your team is guessing on the initial decision
• “Why work my ass off when I don’t know why we’re doing this?”
• Example: “Enterprise customers provide 10x the LTV vs. SMB”
• Context creates clarity, clarity creates commitment

Need a goal system that actually works? I wrote about my struggles with OKRs & EOS, and the system I switched to here (free). I also created an hour-long Masterclass on goal-setting in Highland Academy. There’s 30+ other topics too, with new stuff added monthly!

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Rule 5: Consistently track progress

• Break annual outcomes into quarterly and monthly targets
• Weekly dashboard updates using red/yellow/green status (non-negotiable)
• “Get to Green” becomes the internal mantra (proactive, not reactive)
• Outdated dashboards = operating disadvantage
• Sugar-coating status only hurts the company

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Rule 6: Create accountability checkpoints

• Weekly leadership meetings with goals at the center of the agenda
• Every yellow and red goal gets discussed, prioritized, and addressed
• CEO owns company dashboard; functional leaders own team dashboards
• Same meeting structure every time. Consistency creates accountability
• The meeting forces honesty about what’s actually happening

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Rule 7: Align team incentives

• Tie compensation to goals achievement
• OKR purists are wrong: financial alignment drives focus
• 50% company performance, 50% individual
• Company-wide bonus plan is a great way to do this
• When everyone wins or loses together, alignment becomes automatic

Need a bonus plan structure? I wrote about the perfect plan for any company here (free). There’s also links to the bonus plan Masterclass from there too.

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Go deeper than anyone’s willing.

Don’t let your company drift. Be ruthless about prioritization. Focus on depth of value. You’ll come out 10x better.

Here’s a link to the full article (free) on the 7 essential rules of goal setting.

Till next time,

Never say die 🏴‍☠️

Scot