4 ways managers can help someone launch something new

written by  Ryan Seamons

When you’re working to launch something new, it can be tricky to know how involved to be. How do you balance giving guidance vs jumping in and doing it yourself? Especially when the person you’re managing doesn’t have the knowledge and experience you have? As many a new manager has discovered, delegation is hard.

If you jump in too much, you may get the immediate outcome you want but long term you aren’t enabling someone else to grow. But the flip side isn’t great either. Letting someone completely fail without the support they need can be painful for everyone involved.

So how do you find the right balance?

Case Study: Building a New Business 📈

My most recent example of this conundrum comes from an experience with my 12-year-old daughter.

In our family, we have a theory about how to teach our kids to manage money. 💰

We give each kid a monthly allowance starting at age 6 until age 12. The allowance is twice their age. We give this to help them understand money management, and experience saving (20%) + giving (10%).

But once they turn 12, the money train stops. 🚂

Instead, we encourage and support them in earning their own money.

My oldest daughter planned on babysitting for money when she turned 12 this year. But #COVID.

So she decided to start a new business: the B&B bakery. She would bake breakfast muffins from scratch and deliver them in our neighborhood. She chose chocolate zucchini, banana butterscotch, and morning glory as the flavors.

I wanted her to succeed and learn. But these two outcomes are often at odds with each other.

While she is driven, she’s also fairly inexperienced with most aspects of running a business. For almost every idea she had, I instantly thought of a way to “make it better”. But I also knew that learning was a big part of the benefit she would reap. And to do that, she needed to have a lot of autonomy.

To ensure success, it’s easy by default to rely on the knowledge of the most experienced person. 

To encourage learning, it’s often tempting to let someone struggle and even fail.

Here are 4 things I did to inspire excitement, help her push through the hard parts, ensure she would be successful, and still give autonomy for her new idea:

  1. Ask Questions
  2. Explain Why
  3. Create Prototypes
  4. Run a Retrospective

1. Ask Questions ❓

One of the ways to balance doing work the “right way” and giving autonomy so someone learns is to ask questions. Especially when your first reaction is to tell someone what to do.

The basis of coaching is conversation. Asking questions is a critical piece of successful coaching conversations.

Managers often think they are coaching when they are actually giving advice. (tweet this)

When you give too much advice you actually inhibit learning and reduce motivation.

Waiting for someone to answer is a gift. You’re respecting their thought process.

Also, learning the hard way is how we actually learn. Learning takes work and often involves failure.

Feedback is fuel for learning. And we can’t get feedback if we’re never trying new things or answering questions. Thus advice feels like it’s a shortcut to success, but the problem is that it often goes right around the learning part of the process.

When you don’t give ample time to asking questions and learning, you not only rob someone of the chance to learn through their own mental work, but you also reduce motivation since you’re limiting autonomy.

I asked lots of questions throughout the process of my daughter’s bakery launch.

“When do you think you should deliver the orders?”
“What will someone do after they read your flyer?”
“How can you make sure you won’t mess up the order?”

I often had to wait, even when I had ideas or thought I knew the best answer, so that my daughter could think about the question herself. Once she had gone through the mental work of thinking about and answering a question, then my sharing of advice, ideation, and accountability were much more effective.

Asking questions and waiting for an answer is a critical part of helping someone else build something new.

I had to wait often, even when I had ideas or thought I knew the best answer so that my daughter could think about the question herself. Once she had gone through the mental work then my sharing of advice, ideation, and accountability was much more effective. This is an importart part of helping someone else build something.

2. Explain Why 💬

There are only two ways to influence human behavior: you can manipulate it or you can inspire it.

Simon Sinek

While questions are the basis of coaching, you still need to occasionally give advice when mentoring or managing. There are times when you know something won’t work.

So, what do you do?

You could be purely directive. Push, force, or cajole someone into doing what needs to be done. But without context or explanation, this quickly becomes frustrating.

Repeated consistently, this approach treats someone like they will never learn.

The highest goal of leadership is to create more leaders. And the best way to enlighten while still providing direction is to explain why.

Explaining why teaches and inspires someone about action they should take. It’s an effective way to bring someone along even when you need to be more prescriptive.

My daughter was going to make a mistake.

She wanted to buy nice boxes for her muffin orders. She searched online and found a 10 pack for $15. I asked some questions to try and deter her (since this purchase would eat into her margin completely), but she was pretty set on the idea. I convinced her to wait, but then when we went to Hobby Lobby for some other supplies, she again found boxes, these ones $1 each. As she told me she wanted to buy the nicer box, I paused and realized I hadn’t explained the why well enough.

“These boxes look awesome but for these first orders, I don’t think this will get you what you want. Remember how we talked about margin? Well, if you buy this, what will happen to your margin? If you want nicer boxes, then you’ll need to charge a lot more for your muffins and I don’t think you’re there yet.”

By slowing down to explain the why (and ask some questions) I helped her realize my point and understand more about the concept of margins. She ended up making a cute paper plate hack that worked much better for her margins and her customers loved:

Directions are instructions given to explain how. 
Direction is a vision offered to explain why.

Simon Sinek

One of the hardest parts of managing is knowing when to give autonomy vs when to step in. Explaining why is one way to show respect even when you disagree. Inspire someone to act.

3. Create Prototypes ⚙️

If you are not embarrassed by the first version of your product, you’ve launched too late.

Reid Hoffman

When I started as an MBA intern at LinkedIn, getting face time with company leaders was definitely one of the most exciting parts of the opportunity. This included a few chances to learn directly from Reid Hoffman.

I’m a big fan of many concepts he’s introduced to me (like disrupting the diploma or his suggestions about personal branding from the startup of you). But the idea about embracing embarrassment was the most personally impactful.

People I’ve shared this with either love the idea or immediately start pointing out times it doesn’t work.

“What about medical things where life or death is involved?”
“I work at a company where things have to be thought through first!”
“I’ll get laughed at if I launch something that isn’t ready!”).

But this doesn’t mean your public launch has to be embarrassing. It means that you’ll learn the most when you can put something out before it’s fully polished.

Put another way, your first version is going to be terrible.

So if your first version was guaranteed to be terrible, how would that change your approach? Here are some ideas:

  • Draft an outline for your article or presentation, then talk it through with someone for feedback
  • Test before you launch. The more realistic, the better.
  • Get beta users who realize this is something new and you’re trying to learn (Google had ‘beta’ on Gmail for a very long time)
  • Draw out a model of a website or app using pen+paper or google slides
  • Role-play a conversation or process flow early on
  • Ship a slice of value that helps customers with a heads up about expected next steps

These are ways to “launch” sooner. And make your actual launch come more quickly as well.

Prototypes make it safer to do something for the first time.

There were lots of things for my daughter to prototype before she built the final product and put something in the hands of paying customers. She test build the muffins, the paper-plate boxes, and the flyers before launch day.

I encouraged my daughter to test things herself first, then show someone for feedback.

This helped her to avoid failure (earlier in the week her morning glory muffins sank and she had to adjust the recipe) and make a more effective product (the marketing flyer went through 6 iterations).

But you don’t only prototype products—you can also prototype processes!

She practiced getting up early and baking muffins to see what baking morning would look like. She also tested making the batter the night before. And we role-played the conversation she would have when she talked to someone in the neighborhood.

A prototype helps you learn what reality could be like. Encourage those you manage to create a prototype first. Test runs, first drafts, pilots … all variations can help us learn fast and iterate.

We can often prototype more than we realize.

Bonus points for getting real user feedback about the prototype.

4. Run a Retrospective 📝

We should all be doing more retrospectives.

A retrospective is a short pause for reflection that can be used by a team or individual after a project or at regular intervals during work.

It typically takes 30-45 minutes but can be a shorter discussion too. 

I’ve found 3 simple questions that make for effective retrospectives:

1. What went well?
2. What didn’t go well?
3. What do we want to change moving forward?

The best retros are about building openness and awareness as a team. Get people sharing and listening, commit to a meaningful change, and you’re better than 95% of teams that are either not doing this or just going through the motions.

After the morning of deliveries, we ran a quick, informal retro. This gave space for my daughter to reflect and learn (even with a few eye rolls for having a dad who says things like “Hey, let’s run a quick retro!”).

  1. We celebrated together what went well ($20 on the first run, multiple complements, successful delivery morning).

2. We talked about some things that didn’t go as well (Condensation formed because she didn’t let them cool enough, Dad’s job was to wake her up since she sleeps in the same room as a younger sibling and he almost forgot!).

3. And we started talking about adjustments for the next delivery day.

Retrospectives give space to talk about success, failure, and change in a way that gives hope and can show respect. It’s a clear ritual that signals the belief that we can always improve our work.

How It Ended 🎉

In the end, my daughter delivered 4 orders and made her first $20. She has plans to grow the business by increasing marketing (flyers in the rest of the neighborhood) and offering an additional product for an upcoming holiday (sugar cookie kits for kids).

The best way to learn entrepreneurship and innovation is to jump in with both feet. Start small and put yourself out there. Knowing how to help someone else through the process is tricky. You have to balance giving space for failure with being directive.

It was fun to watch my daughter go from idea to impact in a couple of weeks with a new business. It was hard to not just do things myself at times. But more than the money, I want her to learn and grow.

Asking questions, explaining why, creating prototypes, and running retrospectives are easy ways to ensure success and still give ample autonomy to those you manage.

About the Author

Ryan Seamons
writes about more human approaches to modern management.

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