The difference between good startups and great startups: Planning and Execution

The difference between good startups and great startups: Planning and Execution

Welcome to Forge Ahead!

The Blog for Ambitious Startup Founders

From avoiding founder overwhelm to how to improve your investor readiness, and much, much more!

The difference between good startups and great startups: Planning and Execution

When you are building a startup, it can feel like there are never enough hours in the day to get to everything you feel you have on  your plate.  This sense of overwhelm means that some things fall through the cracks. For many founders, one common casualty is making time to review their strategies and update their operational plans .

Lots of founders make time to create a business plan or think about their strategies and goals when they are preparing their pitch deck.  But many see business plans and pitch decks as something that you create for other people. More than that, they see them as things that you do once as a special project.

The truth is that planning and execution are the lifeblood of startups, and making time to review and update your plan is crucial.  Your business plan should not be a static document. It should be something that you share with your organization and  use actively to build and execute your vision.

You never hear anyone say that investors invest in founders that can come up with great strategies, or founders that have lofty goals. Instead, you hear that investors bet on founders that can execute.  And execution starts with a plan.

It may seem like common sense, but I speak with a lot of founders that don’t have plans they can use to manage the business. They have strategies, like their “go to market” strategy, or their “product development” strategy.  And they have goals, like “we’ll increase revenues this year by X%” or “we’ll expand internationally in 2021”.  But you can’t execute these strategies or goals without a plan.

So what are the required ingredients of a good plan?  Here’s my list:

  • Tactics and actions
  • Deadlines/schedules
  • Progress metrics

There are lots of YouTube videos that include a lot more things, but I want to keep this simple. If your plan includes these elements, you are already doing better than a lot of founders.  I’ll elaborate a little on my 3 requirements.

Tactics and actions

The biggest problem with strategies and goals alone is that they don’t tell you what you need to do day-to-day. To achieve your goals you need the methodical application of tactics and actions.  That can include things like:

  • Contact 40 customer prospects per week
  • Create weekly content targeted to our target market about [insert problem]
  • Negotiate volume pricing for …
  • Review website analytics and launch new A/B tests monthly
  • Develop an email campaign to reactivate inactive customers
  • Poll existing customers on service or satisfaction levels

For your business, what are the daily, weekly, and quarterly activities that you, or members of your team, can do to produce the result you want?  Do you have a list of those activities? Do you know who owns each of them?  Are you tracking that they are being done and do you have a way to track their effectiveness?


Deadlines and schedules are usually the second big gap in startup plans.  Annual goals are a lot like the term paper assignment you got at the beginning of the year. There is no urgency to work on it.  With startups, you need to create urgency around your strategy. That means mapping out a timeline and due dates for your actions and tactics. 

You should break annual goals down into shorter-term milestones, like monthly or weekly.  Some of the actions and tactics will be one-offs, and some will have to be routines. What’s important here, especially as your team grows, is that these actions are coordinated, and that can only happen when you schedule them. 

I see founders who are lax about due dates and deadlines, but you need to treat meeting deadlines as an organizational discipline.  If you are lax at the beginning, that will become part of your culture. As you grow, the organization will be lax as well. And if you make promises to customers and don’t keep your promises as an organization, you won’t be in business long.

Create an organizational culture where deadlines and due dates matter.  It’s difficult to change the discipline of a culture once it starts to set. Setting and meeting deadlines also helps your team coordinate their efforts. CEOs that make and keep promises about what they are going to do raise money MUCH easier than those that don’t!

Progress metrics

I mentioned that goals don’t inherently have urgency, like that term paper. Setting near-term deadlines and incremental milestones helps you create a sense of urgency and manage workflow. It also gives you an objective way to track and measure your progress, make sure that you are on schedule, and let you see if the tactics that you are using are effective. 

The one thing you need to know about plans is “They change”. Mike Tyson famously said, “Everyone has a plan until they get punched in the face”.  Your progress metrics are your way of quickly seeing what actions are working and which are not. If you don’t have progress metrics in place, you risk wasting a ton of time and money on ineffective actions. Progress metrics also gives you the ability to identify problems, adjust your plan, and get back on course.

When something isn’t working, be sure to ask “why”.  Is the tactic flawed? Is the execution flawed? Are we hitting the right audience? Whatever the reasons, take the opportunity to learn from your “why” and adopt new tactics.  Then rinse and repeat.

When you are creating your company roadmap/plan…

  • Start with developing clear and achievable Goals/Objectives
  • Make a comprehensive list of the activities that will be needed to meet those goals
  • Break the goals down into quarterly and monthly goals and weekly deliverables
  • Identify the metrics you’ll need to see to know if things are working as planned
  • Make sure all activities and deadlines have someone who is responsible for them
  • Track, review, and analyze your results on a regular basis
  • Update and adjust your plan as needed

As soon as the organization is more than just you, you will need to have a way to give your team visibility into the tasks, deadlines, and key metrics.  You don’t have to use something sophisticated or expensive. Many founders start with Google Sheets or anything cloud-based that multiple users can see and update. If you wanted something a little more sophisticated, you can easily build project tracking sheets in Airtable or Notion. And lots of project management software, like Asana or Clickup, have free versions to help you get started.

Go forth and execute

Hopefully, you are already doing most of the things in this post.  If not, here’s your checklist to supercharge your company’s execution:

  • Make the time to review and update your plans regularly. Adjust based on what’s working and what’s not. Also consider updates based on: changes in the marketplace; feedback from your customers; and new opportunities that may have popped up.
  • Consider your plans to be fluid and adaptable and visible to your entire team
  • Create expectations for all of your activities.  Track the results early so that you know when to adjust
  • Have an individual responsible for critical tactics, and for keeping activities on schedule.  Let everyone know how their project fits into the success of the company
  • Hold people accountable to deadlines and lead by meeting your personal deadlines

I hope this helps. Go be epic.

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The Best and Worst thing about being a Founder

The Best and Worst thing about being a Founder

Welcome to Forge Ahead!

The Blog for Ambitious Startup Founders

From avoiding founder overwhelm to how to improve your investor readiness, and much, much more!

The Best and Worst thing about being a Founder

In my coaching practice, I run across common questions and themes.  Some of the themes revolve around the question of why being a founder seems way more difficult than you expected.  And while the tech media might make it look like every founder was an overnight success, I want to make sure you know that most of them felt like they were in over their heads for at least a moment.  This post is about one of my favorite reasons why this stuff is just plain HARD!

The best/worst thing about being a founder

Being a startup founder is harder in reality than most people think before they get started.  Some founders are drawn to one of the best parts of being a founder: not having a boss.  The funny thing is that for some founders, not having a boss is also one of the worst things about being a founder.

Let’s face it. Having a boss makes things simple.  Bosses are sort of the Google Maps of work. They tell you what you need to do and when you need to do it. They even tell you the destination that you should enter into Maps.  Sometimes, Maps will give you options on how to get to your destination and will even tell you the difference in the routes (usually in relative time), so that you have a feeling of choice.  But ultimately, all roads lead to the same destination: the one your boss gave you to begin with.

If you arrive at your destination and it turns out to be the wrong destination, that’s not your fault.  Your boss had the responsibility of deciding where you should go. Your responsibility was to get there to the best of your abilities. 

Was your boss doing you a favor?

Bosses provide all sorts of wonderful things that you might never have appreciated.  For example, they often give you deadlines and due dates.  I know what you’re thinking: “deadlines and due dates are wonderful?”  Now that you are a founder, you tell me.  When I work with founders, many of them struggle with two things:  They struggle with setting deadlines and due dates, and then they struggle with staying on schedule once they’ve created them.

It turns out that having someone else hold you accountable to deadlines is often way easier than holding yourself accountable.  Maybe we’ve been trained by those term papers that always had a deadline that some of us barely made.  But when there isn’t anyone to hold us accountable, deadlines often “slip”. That voice in your head says “It’s only a few days…”.

Another “gift” from bosses is prioritization.  What you don’t often realize when you have a boss is that there may be 100 things that you need to get done over the course of the year.  You don’t realize it because your boss is usually the one that decides what you should be working on right now. They’re prioritizing for you. They are looking at everything you could be doing and giving you the filtered list of what you should be doing at any given time.

Too much choice can be overwhelming

One of the last and biggest gifts that you get from your boss are “lane lines”.  Your boss gives you a limited scope of responsibility.  For example, you are responsible for marketing a particular product line, or selling to particular clients, or managing certain people.  When you have a boss, you might crave more. More power, more responsibility, more scope.  As a founder, you now understand the saying: “Be careful what you wish for”.

In summary, bosses:

  • Tell you what to do
  • Tell you what the destination is
  • Give you deadlines
  • Limit your scope

So is having a boss better than being a founder?

Not necessarily.  But having a boss and being the boss are two very different things. You should expect that making that transition can be challenging.  For example, without a boss, we have to take on a host of new decisions that we formerly took for granted.  And those decisions carry the weight of success or failure with them.

For starters, you have to decide: 

  • What the company is going to make…
  • Who the company is going to serve…
  • How the company is going to make money…
  • How it’s going to create its product/service…
  • And a thousand other details that will be the foundations of your success!

These decisions, in aggregate, will become the “destination” you need to enter into Maps.

But wait! There’s more…

Once you decide the destination, you have to essentially build the vehicle to get there.  And this doesn’t mean that you get a box of vehicle parts labeled with instructions like something Ikea would do if they made cars. It means deciding what vehicle you want, determining what parts you need, and how you need to assemble them.  Think “random Ikea parts with no instruction manual”.

Next, you need to set deadlines for this heap of uncertainty.  The first version of the vehicle will be ready by “x” and the destination will be set by “y”.  We’ll assemble a crew in the next 30 days and we’ll get the money for the trip in the next 90 days.

Without a boss, it’s up to you to decide what tasks and projects have priority. After all, you have limited time, limited personnel, limited money, and an unlimited list of things you “could” do.  So you have to determine where your time and resources can be most effectively spent to help you meet your deadlines and get to your destination!

And last but not least, as the founder, you are responsible for all of it. Yikes!  And did I forget to mention that when you have a boss, you don’t have to figure out how to pay for it all or have to find investors?

So if you are wondering why starting a company has seemed harder than you thought, maybe this will clarify things.  You should also know that you are not the only founder feeling like this founder gig is tough.  But, as the saying goes: if it were easy, everyone would do it.

So how do you make it easier? 

Don’t try to do it all by yourself. 

  • Recruit a strong team that can help you figure out the destination and that you don’t need to micromanage  
  • Look for advisors, mentors, and coaches
  • Speak with other founders and find your brain trust
  • Find the types of investors that can help you navigate the decisions, not just give you money
  • Remember that you are going to get a lot of decisions wrong. That’s part of the process.
  • Commit to learning from your wins and losses everyday

Being a founder is tough. It’s an emotional rollercoaster. It’s also very fulfilling when you get it right.  Acknowledge that it’s difficult, make mistakes, and then get it done.  If you find yourself struggling with any of these things, let me know, I’m happy to help.