How to be a great leader: 20 leadership lessons

9 min read
11 Dec 2018

rom setting clear, definable goals, to communicating your vision to the masses, being able to effectively lead your team is an essential building block for long-term success.

This article was written by the original owner of, Ryan Allis, and published on his website in 2012. Read more about why Ryan was happy to hand over his website domain to us here.

What great leaders have in common

Great entrepreneurs and great leaders have one key characteristic in common: a passion for making a difference in the world and a clear vision for how they want to achieve this. If you have taken the time to really figure out what you want to achieve and you’re able to communicate it to others, you already have the most important skill a leader needs.

The other leadership skills you will need can be learned—and the best place to learn them is on the job. I learned everything I know about leadership through trial and error, and through listening to my employees’ feedback. I still have a lot to learn, and I consider developing my leadership skills to be a lifetime project that I’ll be engaged in for as long as I’m in business.

At the end of the day, your abilities as a leader, along with your abilities as a communicator, end up directly impacting your ability to make change in the world and inspire others to achieve great things with you.

20 leadership lessons I’ve learned

1. Make sure you’re passionate about what you are leading your team toward accomplishing. If you’re not passionate about achieving this goal, you’re leading the wrong organization

I’d say this is one of the most important lessons I’ve learned. If getting up that hill is something you’re not passionate about, it is going to be very hard to get up that hill.

If you are not passionate about the change you are working towards making in the world, you need to stop what you’re doing and find yourself an organization whose mission and purpose is aligned with your own.

2. Surround yourself with people smarter than yourself, people of high integrity, and people passionate about achieving the same goal as you

It’s possible to inculcate passion: to take someone who is a highly competent, smart person and share with them, through stories and through your understanding of the world, why you’re passionate about what you’re doing. If you can build a team of these kinds of people, you can often achieve things that you wouldn’t believe.

3. Only hire someone as a direct report if he/she can do the job at least twice as well as you could

If you’re hiring someone to take over as your chief operating officer, make sure they can run the ops of your company at least twice as well as you can. The same principle holds with marketing, finance, product management, customer service, sales, or any other position in your firm.

4. Never have more than five or six direct reports

At one point, I ended up having eight direct reports at iContact, plus a five-person board of directors to manage, which meant that I was unable to fill any of my main roles as CEO well.

A good structure, (for me, at least), is to have someone to run finance, someone to run people (HR), someone to run operations, someone who runs the product, as well as a great executive assistant. The rest of the team should then report to the Chief Operating Officer.

5. Avoid micromanagement

One of the biggest mistakes I made as a young manager was being a micromanager. I would give unclear directions and then come back the next day and suggest minute changes, like adjusting the font size on something. I can only imagine that it was a bit frustrating working for me in those early days.

If you follow the advice of Lesson 3 and hire people who can do their jobs twice as well as you, you won’t need to micromanage them. Your job is to help them set goals and hold them accountable to those goals, but not to interfere with how they achieve them.

6. Make sure you and your team are completely clear on what you’re trying to achieve, by when, what the definition of success is numerically, and why what you’re trying to achieve matters in the world

I find, too often, that team misalignment is the biggest obstacle to goal achievement. Sometimes the reason the team is misaligned is that they’re working towards different goals, or they don’t understand numerically what the goal is in the first place.

Regardless of where in the organization a person works, he or she should be able to point to a printed out piece of paper that has a small number of clearly-defined numerical goals for the entire company, and for their particular department. And those departmental goals should align with what’s necessary for their department to do its part in achieving the company goals.

7. Paint a clear vision with your words and with imagery and communicate it succinctly, visually, broadly, and repeatedly. Know where you’re going, and then lead people there

Your employees’ future—their career and their family’s security—is directly tied to the success of your company, which certainly motivates them to contribute. You want to make sure that your team believes in your company, what it stands for, its mission, its purpose, and its products and services.

To make sure that they know that the hard work that they’re putting in now will likely pay off, you have to not only have a vision, but be able to communicate it effectively as well.

A strong leader is someone who knows where he or she is going and why, and can motivate, inspire and guide others towards that path regardless of the challenges ahead.

8. Align success for the individual with success for the project and the company

This is one of the most powerful lessons I’ve learned. Take the time to get to know your employees well and understand them personally (not necessarily all of your employees if you have many, but at the very least the ones that report to you) and understand what each of their life goals are. What are the next five years of their life truly about?

Figure out what motivates them and what drives them, beyond just financial returns. If you can align success for the individual towards his or her own life goals with success for the numerical goals of your project, you could achieve tremendous results, as you will have unlocked the most powerful force in human nature: intrinsic desire.

9. Ask each team member to identify and train their successor before ever leaving the team, and in exchange you will never surprise them with termination

This describes a two-way commitment between yourself and your direct reports, which you should establish in a conversation with each of your team members at the beginning of their time with your company.

Ensure that each team member who reports to you agrees that before they ever leave, whether it’s retirement, quitting or taking a new job, they will identify, hire, and train their replacement. And you, in return, will give them notice in advance of when you’re even considering letting them go.

I think it’s a two-way street. I find that one of the biggest challenges to companies achieving aggressive goals in the middle to later stages is critical executives leaving during really important times. By inculcating the value from the very beginning that a true leader identifies, finds, and trains their replacement before they leave, you will ensure continuity within your organization.

10. Work on developing the following characteristics in your team, and you’ll be cultivating the future leaders of your company

1.Ability to understand the needs of the customer
2.Ability to create products that solves the customer need
5.Aptitude for public speaking
6.Ability to communicate a vision
7.Ability to authentically care about employees and customers
8.Desire to work hard

11. Ask your team to never let something important go unsaid

It’s important to choose words carefully and not necessarily say everything, but it is important to say everything important—not only for you, but for all of your team members.

Too often I find that employees are afraid of their bosses or their managers—the very people who are supposed to be leading them and guiding them towards success. If an employee is afraid of the person leading them, they will leave out critically important feedback.

The best organizations are not ones where the brains are just at the top. The best organizations are ones where the knowledge, power, and ability is distributed across the whole company.

The best organizations have systems that drive important feedback about products, product development, market research, and customer experience, all the way from the bottom to the top of the organization.

12. Listen and actively seek out information from your team, especially unpopular opinions 

While you might hope that your team will tell you difficult information without you having to ask for it, oftentimes they won’t. You need to be actively seeking out unpopular opinions.

This is especially the case when it comes to expensive company strategy. If your team is withholding data that doesn’t necessarily support the strategy that you might be about to spend millions of dollars pursuing, this could be catastrophic. You want to encourage heretics and people who will think differently than you.

13.  Always take the time to explain the mental math behind your decisions

People will follow a good leader, but people will follow a good leader even further if that good leader takes the time to explain the reasoning behind what they’re deciding.

For example, you could go up to a very talented graphic designer and irritate her by asking her to change the background. But if you ask her to change the background and simply explain why you feel like the background should be changed, she will learn and understand and better be able to predict what you want in the future.

Take time to share your rationale and the thinking behind your decisions, particularly with those you are giving direct instruction to.

14. Commend and praise more than you criticize

Too many leaders are quiet when an employee is doing well, and the second an employee does something wrong, they are all over them.

Aim to have a commendation to criticism ratio greater than three to one. Make it clear that you are not only there to condemn and correct. Encourage and praise publicly and create award systems and pure recognitions systems.

Many people thrive on peer and superior recognition just as much as on money, so instituting a program and a process through which you can ensure that you commend people publicly will enable you to motivate people and encourage their own intrinsic motivations to come to the forefront.

15. Don’t be too serious

Have fun. Make the business environment enjoyable. We spend too much time at work for it to be boring. Nothing can beat the effects of a company outing or a celebration after reaching an important milestone.

Encourage practical jokes; encourage laughing. You want to have your own maker time where the engineers and developers can focus and be in the flow, but you also want to have time to celebrate and come together, build community, and have fun. Finding that right balance is the goal of a good leader.

16. Work hard alongside your team

Make sure your employees see that you are there and that you’re working with them. No one likes to work hard for someone who doesn’t work hard him or herself, especially early on.

Be the first to arrive and the last to leave, whenever possible. You, as the leader, are likely to have a tremendous amount more of economic incentive to make your company succeed. At the very least, make sure you’re there and committed as much as your team, if not more.

17. Make sure everyone knows that they can talk to you anytime

You should be available for your team, and let them know that they can talk to you anytime. Keep your door open, or at least have a scheduled block of time when anyone can come chat with you. Make sure people know you’re accessible and that you’re approachable about any problem that they’re having.

18.  Treat people with respect at all times.

This is one of the most important lessons. It’s the Golden Rule applied to business. Treat people with respect at all times whether they be employees, customers, suppliers, or partners.

19. Consciously build an amazing business culture

At iContact, for the nine years we were building the company, we truly worked to build a family culture. When someone was moving into a new house or needed a ride home, we did our best to create a culture where we there to help, particularly in the early years.

We worked on building people up. We created five values that we called “WOW ME” which stood for Wow the customer, Operate with urgency, Work without mediocrity, Make a positive way, and Engage as an owner.

Now, even after I’ve left iContact, I still remember what that acronym means off the top of my head. It’s very important to create a set of values that everyone in your company remembers and to take time to celebrate your victories together.

20. Keep learning from people who’ve walked the path ahead of you

It’s too easy, as a leader, to feel like you have to be the one who knows everything. Great leaders recognize that they also need to learn, and they create opportunities to do so.

Surrounding yourself with individuals much more experienced than yourself, who have already achieved what you want to achieve, is critical to your ability to quickly learn what you need to learn in order to succeed in building your business. Create an advisory board, or form relationships with mentors who have integrity, experience, and wisdom.

*This article was originally published on October 17th, 2018 and updated on December 11th, 2018.