Week 1 - Everything I Needed to Know About Managing a Team in a Small Business

Here is Week 1 of the 52 Week series in my 2018 Year of Learning. In this week, I cover 6 articles and learning resources I consumed concerning Managing a Team in a Small Business.

Come back next week to see what I learned about American Real Estate.

Getting promoted to a manager role can be scary, especially since many people (including myself) experience the impostor syndrome - where you don't feel qualified or prepared for the role that you were promoted in to.

The shift from a member of the team to the leader requires you to not only look at how you interact with people but also how your impact on the company has now changed. While you can't control everything that is happening, you have been placed in a role that can do more for your company, and it is up to you to lead your team into delivering something fridge worthy (a Direct Development core value).

To manage and lead people effectively, you need to know them personally. This can be as simple as going for walk, grabbing lunch or coffee, or just having a one-on-one meeting with them. The goal is not to evaluate them as an employee, but to know them as a person. By doing this, you can better shape your management style that works with your employees and pushes them into areas that they will thrive in.

The enemy of good management and leadership is ambiguity. Don't let it creep into your relationships and undermine your position. Make clear goals and stick with them, and make sure your employees are clear on what they are and why they are important.

These goals help your employees understand why they are doing what they are doing. They shouldn't just be completing tasks, they should be analyzing situations and making the best decisions with the knowledge and resources they have. As the manager, you need to delegate and prepare your employees to do their job effectively.

Sometimes this means giving them a step-by-step explanation, and other times it's letting them experiment. By meeting them halfway, you are developing them as leaders, which you will need them to be as you gain and delegate more work.

Having a team of people that are confident in the decisions they make effects how you perform as a company in the long run. You don't want to be a manager that is only reactive and not proactive. Being proactive allows you to look ahead and prepare for what's coming, instead of just trying to play catch up or disaster relief.

Make sure that you rely on other managers who are around you and learn from them. Sharpening yourself on them will ensure that you stay ahead of the game and keep building a stronger team.

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In this article, Entrepreneur talked with 32 businesses and asked them for advice, tips and best practices when it comes to running a small business and managing a team.

I won't just list all 32 pieces of advice, partially because I would just be copying the article, and partially because some of them are just weak. So, I'll just highlight seven of my favorite quotes and how I've seen their importance in my own life.

Rehabilitate all micromanagers……or replace them if you can’t save them……because they will kill all autonomy, creativity, and risk-taking and force your best people to leave.
— Chris Licata, Blake’s All Natural Foods

What I like about what Chris said was just the absolute confidence in his statement. He's clearly speaking from personal experience and I totally agree with him, mostly because I tend towards the micromanagement myself. I really struggle to give important tasks to other people because I have a hard time thinking that they will do as good a job as me. And this is such a deep flaw in not only my professional life but my personal one as well.

I think Chris really spoke truth here. Having micromanagers try to control everything only inhibits your team’s success and sets your team and company up for failure. Here's to a year of more trust and less micromanaging.

Never be afraid to ask for help.
— Jan Erickson, Janska, LLC

I have always hated asking for help. And I think this stems from me thinking that I'm smarter than I am, and a fear that if I need to depend on someone else, then they will let me down. After two-plus years at Direct Development (DD) though, I know that asking for help is something that can never be downplayed, and those who ask for it are smarter than those who don't.

Asking for help was something that I did very little of when I first started, and it showed when I would spend hours in HubSpot trying to fix something by myself because I didn't want to contact tech support. All those wasted hours helped me realize how limited I am in my expertise and the need to seek the knowledge that my peers can lend me.

Trust your gut instinct BUT always back your gut decisions with data.
— Max Kothari, Express Kitchens

Our CEO, Tony Fraga, constantly says that everything we do internally and for our clients needs to be backed up with data. I think him and Max would really get along. I really liked this quote not just because I agree with it and my boss says it every week, but also because it is something that I focused on in my senior capstone at George Mason University.

With all our clients on HubSpot, we have massive amounts of data at our fingertips, and we barely have time to go deep into it. But the data we do have, we use to make sure the decisions we make have a solid foundation.

Leaders must be close enough to relate to others but far enough ahead to motivate them.
— Dr. Amir A. Varshovi and Marla K. Buchanan, JD, Green Technologies

This was my favorite quote out of all 32 that I read. It really speaks to the confusion I felt when I was promoted into a manager role and didn't know what the hell I was doing (looking at you impostor syndrome). It is both scarily specific and wonderfully ambiguous on what you need to do, and I believe points me in the right management direction that I want to go.

Make sure team members understand the Cause and Mission.  If they embrace it, they will be stellar team members.  If they don’t, get rid of them sooner than later!
— Ryan McFarland, Strider Sports International, Inc.

As a manager, I get to have some open and honest conversations with a handful of employees, from marketing techs to content writers. One thing I kept hearing when I talked with them was that there was just a general desire for seeing the bigger picture. This can be seen both in your daily/weekly/monthly projects as well as the mission statement for your company.

People want to see that bigger picture and be brought in to help shape it, and when you give them that responsibility and stake in it, they will want to thrive too. Humans, at their core, are creators. Enable your employees to help create something, and it will benefit them and your company down the road.

Great ideas are a commodity, great execution is not.
— Harvey Nix, Proventix Systems, Inc.

Short and sweet, like myself. Something that we have a lot of at DD are great ideas. Something we don't have a lot of is great execution of those ideas. We've hired a lot of really smart, creative and passionate people in the past year. And while we can spit out some awesome ideas, we haven't found our rhythm yet on turning those ideas into realities. I really liked this quote because it hit close to home (shout out to the DD podcast).

Make sure you’re not the smartest one in the room. Surround yourself with folks that have ‘lived in the future.’ They aren’t afraid of the growth because they’ve been there.
— Michelle Kerr, Lightwell

This one caught my eye because I've heard it somewhere before but can't remember where. And it relates to my lifelong journey of realizing that I don't know as much as I think I do and that relying on others might be a good idea. The workplace that I hope to build and work in is one that allows people to really express their ideas but then not take offense when someone pokes holes in that idea.

It reminds me of what Ed Catmull said at Inbound 2017, and while not exactly referening the same point, I think there is a lot of overlap. Since I don't have the actual quote, I'll just give you the gist. Essentially, Ed talked about how whenever employees would come to the group with an idea, they were mature and trusting enough that when people started to shred that idea, that they would know it was for the better of the company, that person, and the idea itself.

Being able to challenge a co-worker's, or even boss' idea takes a lot of trust, and that is something that I hope to have as a company one day.

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According to the Harvard Business Review, the defining role of a manager is to "boost the engagement levels of the people who work for them." I like this definition because it's not the first role I think of when describing my role as a manager, and is something I wish I did more of at DD.

The main meat of this article though was something that all great managers have in common - a rejection of "conventional wisdom in four core areas of managing people: selection, expectation setting, motivation, and development." These four areas are actually referenced by Curt Coffman, the author of First, Break All the Rules: What the World’s Greatest Managers Do Differently.

In selection, the best managers hire people who have real talent, not just people whose skill set match the job description (conventional wisdom). This talent is seen in employees who are somehow redefining how their job is done each day, not just finishing tasks and meeting deadlines.

With expectations, it boils down to knowing that you hired a talented person and that by giving them a clear goal, you don't need to give them a step-by-step instruction guide on how to achieve it (conventional wisdom). By just giving the employee a clear goal, they can use their skills and talents to achieve that goal, without the need for any hand-holding.

Concerning motivation, conventional wisdom tends to say that managers need to find their employees weaknesses and then somehow fix them. Great managers, however, focus on their employees' strengths and help refine them, while also implementing strategies to support their weaknesses. Great managers leverage what people can already do well.

And finally, with development, it can really be summarized like this: "Conventional managers rate the person and develop the performance; great managers rate the performance and develop the person."

As someone who has worked under great managers, I can say that they do rate performance and develop the person. I have been given numerous opportunities at my job to develop myself professionally, both through promotions but also through various workshops, conferences and online education platforms that my managers encouraged and allowed me to pursue.

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Step 1. Outline Your Goals

Everyone should have goals in their life. These goals are what we are trying to achieve, whether personally, financially, academically, the list goes on and on. This is no different when it comes to the workplace. Setting goals for the team that you manage means that they now know what they should be striving for.

Having the goal promulgated means that employees need to do less wandering, and even though not all who wander are lost, it sure is a hell of a lot more helpful if you know where you're going.

Step 2. Determine Where You Want to Improve

Every team has weaknesses, and these weaknesses should not be kept in the dark or shoved under the rug. If you can't do something that day, say you can't. If you don't think you're the right person for a certain project, tell the manager and suggest someone who is.

Knowing your weaknesses means you can begin a journey to improve them, and as a manager, I'll take any employee that is willing to find their own weaknesses and let me help them grow in those areas. That honesty and commitment to growth is a key part of every manager's dream employee.

You can begin finding your weaknesses (and strengths) just by taking a few tests, like the Myers Briggs personality exam, StrengthsFinder, or HubSpot's Career Assessment quiz.

Step 3. Talk to Your Team

Probably beating the dead horse here, but communication is important when it comes to any interaction being living entities. As a manager, it's not only your job to make sure your employees are moving projects along, but also to make sure that they are being nourished and developed.

Make sure you talk with them to see areas that you could improve on as a manager, whether through anonymous surveys or chatting during coffee breaks. Even though it might be a little awkward at first to ask them how you could be a better manager, you'll get better answers from asking them than just from reading a book (but books are still important!).

Step 4. Get Organized

All great managers know how to stay organized. If you have recently been promoted to a manager role (like myself), you might be dealing with a lot more projects than you previously had been working with. That means it's going to be much easier for items to fall through the cracks.

Take the first step as the manager and find these areas of disorganized chaos and turn it into...organized chaos. It's still better, right? It could be as easy as setting some reminders on your calendar or finding some easy-to-use organization software.

Step 5. Take a Leadership Course

I'd like to think that once I graduate college, I don't have to worry about going to class or doing homework anymore. But then again, that would make life boring and stagnant.

Learning on the job and in your free-time is a surefire way to broaden your skills, improve your job performance, and boost your value at the company. For managers, it could be better ways to manage teams, how to communicate more effectively, or even understanding different leadership models.

There are a metric butt-ton of resources to learn all these things and more, you just have to start learning.

Step 6. Read Management Books

Along the same vein as taking a leadership course / just overall learning, books are a tried-and-true way to keep your brain and skills sharp. You're not going to be an expert in everything you do, so why not read about the people who are experts in their fields.

Step 7. Learn How to Listen

Ah, listening. Something I probably do too much of.

Working in a small business, I don't think this is gotten to be too much of an issue yet, but sometimes, employees feel like they aren't heard or their opinions aren’t taken seriously by leadership.

As a mid-level manager, I have the opportunity to meet with employees every month and have them explain all their qualms and victories with me. I am then able to bring many of their fears and pain points to our high-level managers and work on changing different aspects of the company and its inner-workings to remedy those pain points.

Step 8. Practice Praising and Rewarding

Praising and rewarding, something I definitely need to do more of. Around two, maybe three summers ago, I was living with a friend’s family and they all decided to take the Love Languages quiz. Turns out, the love language that means nothing to me is Words of Affirmation. So basically, I don't really understand why people need to be praised.

Understandably, this makes it harder for me to do it as a manager, though I still try because I know a lot of people where Words of Affirmation are the first and best way that they feel appreciated. I don't know if this is crossing a line, but maybe having your employees take this quiz can be helpful in your quest to finding how to support them in the way that is most helpful for them.

Step 9. Find a Mentor or Coach

We've recently started a mentorship program at DD, mostly for people who have been recently hired.

It's important to have an outside perspective when it comes to your personal and professional life. People who aren't (or at least not too) personally invested in you are able to give you honest and unbiased feedback when it comes to how you could improve. Plus, mentors are full of wisdom that can help you navigate the stormy waters of your job since they have probably experienced something like it before.

Step 10. Learn How to Effectively Communicate with Anyone

Pretty much a no-brainer, though I will point out the four types of communicators:

  1. Thinkers

  2. Socializers

  3. Directors

  4. Relaters

The actual names for these four may change depending on what source you are looking at, but the basics are consistent. Feel free to learn about them on your own, though their names are fairly self-explanatory.

Step 11. Be More Transparent

People like transparency because people like trust. If you're not transparent with your employees, it's going to be harder for them to trust you. When you as the manager are transparent, your employees are more likely to be engaged in their work and look more favorably upon you.

Step 12. Create a Feedback System

Like our mentorship meetings, giving a place where employees can feel like they can express their views and opinions and then actually be heard is a great asset to company culture.

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Oh man, another listicle. If you're reading this right after the 12 Step piece, feel free to skim. Since this post is already super long and 99% of you probably won't even read this, I'll just start making these pretty brief.

1. Management can be lonely.

In most teams, there is typically only one manager. Because of that, when you hit a wall or experience frustration, there aren't as many people to go to that can remedy that. You must go out and find them.

2. You stop practicing your craft.

Management is a new job, one where you won't be doing the work that you were doing in your old job (or at least a much smaller amount). Take my promotion from a Marketing Technologist to a Marketing Technology Manager for example. I can no longer spend hours trying to debug and fix things because my time is being used elsewhere. Therefore, my web-development skills are getting put on the back-burner because of this job promotion.

3. GSD turns into GTD.

Get Shit Done turns into Get Talking/Thinking Done. Your day now revolves around meetings and strategizing, instead of concrete task completion. 

4. You don’t get as much feedback.

As a manager, you become the person who gives feedback instead of the one who receives (though you still receive it, just not to the same degree). Since you are now doing more Thinking and Talking, it's harder to get more concrete feedback on a meeting vs. when you are executing a launch or building out an integration.

5. You have to do hard things (and you still have the same feelings).

As a manager, you must make a lot of decisions, and sometimes these decisions mean feeling crummy from time to time. You must criticize and correct people, and it might require some tough skin to do it well.

6. Management is emotional.

Management means dealing with people, and a lot of the time emotion gets involved. This means that at times, you must make some tough decisions and receive some harsh words from employees and even friends.

7. Self-regulation, all day, every day.

How you take good and bad news and express it to your team directly affects their performance. As their manager, they look to you for guidance. Your body language and actions tell them how they should react. Make sure you take bad news in stride and make it clear that there is still work to be done.

8. You spend less time in the spotlight.

Since you are managing a team, no success is one person's accomplishment. Teams are designed to collaborate and build on each other. So, don't get butthurt when people don't recognize you individually.

9. You’re the “sh*t umbrella.”

When the shit hits the fan, you need to make sure you have your umbrella ready to keep if off your team. This essentially means doing the work that allows your team to focus on their task at hand. Sometimes it's not pretty, but as a manager, it's your duty to make sure your team can accomplish their goal.

10. Your relationships change.

When your company promotes internal people into management positions, it will most likely make your old relationships a little awkward. Just clear the air and get your relationship back on path, factoring in the new variables that come with a higher position.

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I took a little bit of a different approach with this resource and decided to just show the notes I took while watching this course. Since it is mostly bullet points, I hope that it is easier to consume, though the trade-off being less context for each point. 

Leadership is no longer doing work (per se), instead, it is:

  • Helping

  • Facilitating

  • Structuring

  • Planning

Establishing Identity

Look like a leader

  • Dress code might change (don't do a drastic wardrobe change)

Develop professional relationships (not friendships)

  • Professional relationships focus on performance, which personal relationships can muddy

  • Professional relationships should still have personal aspects

Stay visible

  • Spend 10% of your time each day to just chat with your team (not a meeting or formal sitdown)

  • Send out weekly updates, accomplishments, milestones, etc.

Clarify Performance Expectations

What are the boss' expectations of you?

What is the bigger picture?

Discuss personnel changes

Request needed resources

Meet with team

  • Discuss performance

  • Accomplishments

  • Goals

Team Goals

  • Set Milestones

  • Assign responsibilities

  • Schedule 1 on 1

Define Team Norms

  • When someone is late to a meeting, they must give $1 to office coffee/snack fund (we'd have thousands of dollars each month if we did this...)

Building Rapport

  • Understanding and appreciating your team members

    • Bring personal aspects into conversations and get to know them as individuals and not resources

  • Projecting - Assuming others think and feel the same way you do (big mistake to do)

  • Just show respect

Making Decisions

  • Autocratic - You make a decision and then inform team

  • Collaborative - You discuss with the team and then make decision

  • Democratic - Everyone has equal say in decision

Own your decision

  • Be clear, honest and sincere

Status Bubble

  • Address new status

  • Seek feedback about your performance

  • Encourage positive debate

Servant Leadership - Serving the people you lead to build and develop them

  • Commit to employee development (professional and personal growth)

  • Listen effectively

  • Feel empathy - To understand and be sensitive to other's feelings

  • Promote healing - laugh apologize, admit wrong, be positive, etc.

Increasing Authenticity

  • Be open (in decision making and as a human)

  • Maintain flexibility

  • Be humble (ask questions, promote others over yourself, share authority)

  • Be a role model

Proactive Communication

  • Look for nonverbal cues (eyes and forehead)

  • Ask questions to pursue clarity

  • Predicting Challenges

    • What are hot-button issues?

  • Candor Vs. Civility (both are important and should be mixed)


  • Good feedback is specific, delivered positively, and given in the right amount

Knowing When to Have a Meeting

  • When in doubt, do NOT call a meeting

  • Five Justifications for a Meeting:

    • Important team decisions

    • Major announcements

    • Kick-Offs

    • Premortem - everything that might go wrong over a project's lifespan

    • Postmortem - what we learned and how we did it

Who Should Attend a Meeting

  • Experts, Affected, and Sponsors

  • Rule of thumb: the fewer, the better

Effective Meeting Rules

  • Arrive on time and be prepared

  • Clarify goals and scope (agenda)

    • Avoiding scope creep

  • Be critical but positive

  • No interrupting others

  • No electronics

Strive for consensus through discussion

Meeting Tools and Roles

  • Agenda (create and stick to it)

  • Parking Lot - a place to capture important work-related topics (to be reviewed later)

  • Homework

  • Roles

    • Facilitator

    • Scribe

    • Devil's Advocate

Assert Authority

  • The legitimate right to exercise influence and make decisions

  • Start with a small and measured target, and scale up

  • Make a pro-employee change

Developing a Lieutenant

  • That can stand in for you

  • Mobilize support (act as a catalyst)

  • Get team feedback (unfiltered)

  • Personal devil's advocate

  • Succession Plan - won't get overlooked for promotion because your lieutenant can replace you if promoted

  • What a Lieutenant is NOT:

    • A clone

    • A yes man

    • An enforcer

  • Develop Lieutenant:

    • Bounce ideas off

    • Offering stretch roles

    • Delegate tasks

Coping with Transition

  • Seek support from family, peers and outside network (mentor)

  • Schedule vacation time

  • Get organized

  • Diet and exercise

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If you've made it down this far, then congratulations! I hope you enjoyed what I learned and the small snippets of my job that I tied into many of these articles. And while the week is over, and I am moving onto a new topic, management will continue to be a majority of my life due to my job and will keep on the path of learning.

Too Long; Didn't Read

Being a manager is both about managing work and people. The 6 resources I consumed all had core practices in common. In order to be an effective manager, you need to inspire, lead, and develop your employees. How you do that is up to you. Most people feel unprepared for this new position, but when it comes to managing people, its important to maintain authenticity and seek the good of your team, who will then seek the good of the company.

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