Why Waiting Until You Are Sure Is the Real Risk (And what Jennifer Dodd does instead)

Jennifer Dodd is Chief Executive Officer and Board Advisor of Main Squeeze Juice Co., a cold pressed juice brand with 25 locations and a home office in New Orleans. She has spent about 30 years in restaurants. She started at Wendy's at 15, spent six years at Hardee's and seven at Arby's, where she went from assistant manager to the executive team by the age of 28. Then came Applebee's International, Dunkin' Brands and Tim Hortons, where she ran US development. She has taken brands into 13 countries on three continents.

I built 720 Sweets from one shop to seven locations, then sold it. I hosted speaker interviews at Workstream's On the Clock 2026 in Atlanta. Jennifer's session was recorded at the same event. It is the one I keep going back to. She starts with a story from a first grade classroom and ends by telling operators to stop waiting.

The red F and the second sheet of paper

Jennifer's first grade year included a stretch of homelessness. She describes a childhood of hardship and abuse, and a father whose own childhood was worse. School was where she found hope. She was a straight A student and she worked at it.

One week the family had nowhere to live. She had been bullied the day before for being dirty and unable to brush her hair or her teeth. The next morning she went in wearing the same clothes, and hungry, because there was no school breakfast then.

Her teacher, Miss Montgomery, handed out a coloring sheet to finish before nap time. The picture was a happy little girl with a puppy, a swing set and a home.

She looked at it and gave up. She picked up every crayon her hand could hold and scribbled the whole thing out. A couple of the tips broke. Then she went to lie down.

Miss Montgomery called her over to the desk. On the bit of white she had left, there was a red F.

The F is what jolted her. She had never seen one on her paper. She stood there with her arms crossed, ready to be difficult, and would not explain herself.

So the teacher tried something else. What color would the dress have been? Yellow. What color would the puppy have been? Piece by piece, in a low and hopeful voice, she walked a six year old back through the picture. Then she brought out a clean sheet and fresh crayons, and asked if she wanted the chance to do it again.

She said yes. She sat down and made something she still calls a masterpiece, and years later she understood what it had done. It helped her hold on to a future she could not yet see.

She was about 30, and already a restaurant company executive, before the memory came back. She drove home to Alabama to say thank you. Miss Montgomery had already died.

"We need somebody to step into our life and say, I see greatness in you."

Jennifer Dodd

The rest of her advice comes back to that moment. People show up having the worst week of their year, whether they are six years old or 66. What changes the result is someone telling them what they are good at, and then handing them a second sheet of paper.

Why she decides before the plan is perfect

Jennifer was asked on stage whether she would rather move at 90% ready than wait until a plan was perfect. She has believed the answer for more than 20 years, and her reason is simple. She likes to win.

Winning, to her, is not the deal or the sales number. It is standing at the top of the summit with the people who got you there. Shareholders are happy. Investors are happy. The team is happy, because they can point at the part they did.

Then the warning.

"If you sit around overthinking it, I think that your competitor will pass you by."

Jennifer Dodd

She adds one more thing straight after, and most operators need to hear it. You cannot do this recklessly. It still takes being thoughtful. Moving at 90% is not the same as guessing, and the next two sections explain the difference.

Give the team room once the goal is written down

Most operators skip the condition that comes with moving early.

Her condition is that the company already knows where it is going. Core values, mission and vision, written down and in front of people. Not a plaque on the wall that nobody reads. They have to work, in her words, all the way down to the frontline employee and all the way up to the board.

Do that, she says, and everyone knows what she calls true north, which is simply what success looks like. So when somebody you handed a decision to takes a route you would never have chosen, they still finish at the same result. The leader's job is to keep everyone agreed on where the business is going, not on how each person gets there.

Her example is grass. You want the grass green. You would put in a sprinkler system and use a particular fertilizer. Someone on your team would rather carry buckets of water, because they think they can control where the water lands. That is fine with her, as long as the grass ends up green.

She applies the same rule to suppliers.

"You're my partner. I chose you for a reason. Bring your best thinking to the table."

Jennifer Dodd

Leaders who over correct and over control, she says, take the power out of their own teams. That is a hard sentence for an owner of two or three shops, because over controlling is exactly what got the business open. It is also the reason the third shop never quite runs itself. Leadership at a franchise is a different job from running one, and the switch is mostly about what you stop doing.

A manager can only move fast if the rules are written down. Someone who has to stop and ask whether something is allowed is not running the shift. Workstream's HR platform keeps the policies, records and sign offs in one place, so the standard is the same whoever is on. Explore Workstream →

Keep each mistake small enough to afford

Jennifer's phrase for this is fail forward, fail cheap.

Failing forward means people are going to make mistakes, and that is accepted. You made a mistake. You did not sit still while everybody else got to the summit, measuring and re measuring. Now try not to make that same mistake again.

Failing cheap is the half that puts a limit on the mistake.

"I'd rather you fail in baby steps than a massive leap."

Jennifer Dodd

She is specific about what keeps the steps small. Good systems. Good processes. A board structure that approves the things that need approving. Those are what stop an ordinary mistake from becoming one that closes the business.

A two location owner has all three in cheaper form. The system is a written process for the thing you are testing. The approval is one person you have to tell before you spend over a set amount. Set the amount low enough that a failure is annoying and not fatal, and you can afford to try ten things a year.

People take risks when being wrong is not punished

None of this works if being wrong costs somebody their job or their reputation.

"It's important for people to know that you're a safe place to land, as a team and as a leader."

Jennifer Dodd

She gives private equity the same advice. Let people try things, because the brands that break away from the crowd are the ones that were allowed to try.

Feeling safe is not all of it, and she is clear about that too. The teacher in her story did not only offer a clean sheet. She marked the work honestly first, and then reminded a six year old that she was normally a straight A student and that her coloring was beautiful. The order matters. Hold people to the standard, remind them what they are good at, then give them the second sheet.

She says leaders get to do the same thing for adults every day in the restaurant business. Hold people accountable. Tell them they are incredible and mean it. Watch them get excited about something they thought they had already failed at. Do that honestly and, in her words, the business succeeds and so do the people. That is a better description of culture on an hourly team than most of what gets written about it.

What this means if you run 2 locations, not 25

• Write the goal down. One page. What you sell, who for, and what good looks like. Without it, handing over a decision just leaves people guessing.
• Set the limit before you test anything. Name the most you are willing to lose on one experiment. A loss you can afford is the only kind you can repeat.
• Pick the one decision you are still holding. Hand it over this month, and judge the result rather than the method.
• Mark the work honestly, then offer the clean sheet. In that order. The second chance means nothing if the first mark was soft.
• Assume you are being passed right now. Somebody in your market is already moving at 90% while you get to 100%.

The reason to copy any of this is not that Jennifer runs 25 locations. It is that she was a six year old who was handed a second sheet of paper, and she has spent 30 years handing them out.

Frequently Asked Questions

Is it riskier to move at 90% ready or to wait until a plan is perfect?

Waiting is riskier, because the market does not pause while you check your work. Asked whether she would rather move at 90% ready than wait to be perfect, Jennifer Dodd said a competitor will pass you while you overthink it. She has held that view for more than 20 years. Her one condition is that the move is thoughtful rather than reckless.

How do you give a manager autonomy without losing control of the result?

Agree the result first, then let the manager choose the method. Jennifer Dodd describes a leader who wants green grass and a manager who would rather carry buckets of water than fit a sprinkler system. The method is the manager's business as long as the grass ends up green.

What does failing forward actually mean for a small operator?

Failing forward means a mistake is allowed once and not twice. Jennifer Dodd's rule is to fail in baby steps rather than a massive leap, so any single mistake stays cheap. Good systems, good processes and an approval step are what keep a normal mistake from becoming a fatal one. Her phrase for it is fail forward, fail cheap.

How should a leader respond to someone who is not performing?

Name what the person is good at, hold them to it, then give them another go. The teacher who gave Jennifer Dodd a red F at six years old did all three in a few minutes. She marked the work honestly, then put a clean sheet of paper on the desk. Accountability came first and the second chance came after.

What makes a team willing to take a risk at all?

Knowing the leader is a safe place to land. Jennifer Dodd says people need to hear that before they will try anything, because the alternative is a team that measures and re measures while everyone else reaches the summit. She also wants a shared goal, which she calls true north, because a safe team with no agreed goal still goes nowhere.

Request a demo of Workstream →

About the author. Wilson K Lee built 720 Sweets from one shop to seven locations and sold it. He now runs wilsonklee.com, where he publishes real numbers and playbooks for food and beverage owners, and he hosted the speaker interviews at Workstream's On the Clock 2026.