5 Mistakes You’re Guaranteed To Make As a New Leader And How You Can Recover

Quick Tips / September 26, 2019 / Kristie

Starting a successful small business means that at some point you’ll need to hire and manage your first of one or even several employees! Team management and, more importantly, leadership, is one of the keys to achieving success in your business.

animated businessman at desk with macbook and daylite crm

If you’re a first-time manager, you’re bound to make mistakes – it’s a tough job and you can never stop improving! But you can do your best to recover from some common pitfalls that many first-time leaders encounter. Recently, we had the pleasure of attending the SaaStr Europa 2019 Conference in Paris where Jane Kim, CRO of CircleCI, lead her session The 5 Mistakes New Leaders Make and we’ve outlined what we’ve learned below! We’ve found ourselves guilty of making all of these mistakes, so we also grilled our VP of Marketing, Kristie Holden, on what she’s learned over the years. The good news is that once you’re aware of these pitfalls, you can self-correct and get yourself on the path to being the best leader you can be! 

You will micromanage 

The horror! Nobody likes a micromanager, but it’s easy to fall into the habit when it’s your own small business on the line. It’s your baby! It’s easy to understand why you want things to be perfect and have your finger on the pulse at all times. That said, stop it! Not only is your team perceiving your behaviour as a lack of trust and confidence, you’re also leading yourself down a path of burnout, inefficiency, and becoming the bottleneck in the success of your own business. 

To recover: Invest the time in getting to know your team and how they work. Focus on understanding their strengths and weaknesses – leverage those strengths and work on ways to support them in their weaknesses. Ensure they’re a part of their own development and empower them to use their skills and expertise; their success is your success and vice versa. Don’t forget to start with “why.” Giving your team context about what you’re trying to accomplish will allow them to make decisions based on the bigger picture rather than going off-course or not following the processes you’ve set because they don’t understand your reasoning. To build this habit, we recommend Start with Why: How Great Leaders Inspire Everyone to Take Action by Simon Sinek! 

“Giving clear expectations and clarity on what success looks like has been a learning experience. If you’re not defining what success looks like clearly enough and having the employee repeat back to you what they grasp, then you’re setting them up for failure because you’re not aligned on the outcome. If you align on the outcome, then you can give them autonomy to figure out how to get there on their own and instead be there more for support if and when they get stuck, as opposed to micromanaging.

“Another thing that’s helped is having the right processes and tools in place so you don’t have to micromanage. For example, I use the Kanban Boards plugin for Daylite to prioritize work for our Graphic Designer, Alvina, so I don’t have to check in with her every day to ask what she’s working on or if it’s done. I can just delegate it in Daylite, prioritize it on her board, and get notified when it’s done or when she’s waiting on my feedback.”

– Kristie Holden, VP of Marketing

You will hire the wrong person

You will always need to do your due diligence when hiring, especially if you’re a first-time manager with little or no recruitment experience. You’ll need to take the time to do your research, whether you decide to hire on your own or use an agency. There are several goalposts you can set to ensure you’re investing in the right person but, eventually, you will hire someone who just isn’t a good fit. Once you accept this, you can instead focus on how to course-correct when it does happen. 

To recover: Know your core values and learn to recognize when it’s not a good fit. Define your key performance indicators and ask yourself if this team member is consistently meeting the expectations you’ve set. While you should always be willing to work on developing and training your employees, you need to focus on the health of your overall team – solely focusing on one person’s improvement is a disservice to everyone else. 

“I’ve learned you have to be disciplined in the first 90 days with a new employee. Ask them at the end of each day, “what did you learn today? Do you have any questions?” Based on what they tell you each day the first few weeks, you’ll be able to spot indicators of whether they’re a good fit or not. We’ve also learned that by having a Performance Scorecard it’s easier to identify if they’re an underperformer early on. Each month you can track if the new hire is meeting their KPIs or not and if they’re improving fast enough that you’re confident they’ll be consistent at reaching and exceeding the expectations in your company. One of the things mentioned at the SaaStr Europa 2019 Conference was that the performance of an employee during the first 90 days will look the same at day 900. So pay close attention during the first few months of a new hire!”

– Kristie Holden, VP of Marketing

You will want your team to like you

Everyone wants to be liked! It’s just human nature and it’s totally fine to feel that way. It’s definitely fun to be the cool manager that everyone loves! While you can certainly keep that as a larger goal for your management style when it comes to your interactions, the problem is that when you’re too focused on your team liking you instead of respecting you, you’ll make decisions to be “nice” to your team even though that may not be what they need. Eventually, you’re going to have to make a decision that they don’t like, but it will be the right decision for your business. 

To recover: Remove your ego from your vision of success. Not everyone is going to like you all of the time. You’re going to have to make tough calls and having to say “No” will happen often. Your team may not like it, but if you explain why this decision is best for the business or why you can’t do it as a company, the context can help them understand your decision-making process. Remember to differentiate between “No” and “No, not right now.” It may not be a good time at the moment, but you can always save ideas or feedback for a better time in the future. You can work on a process for your team to share ideas – the answer may be “not right now,” but you can revisit these ideas later so your team knows that you take their feedback seriously. Ultimately, your team may not like you at the moment for the decision you’ve landed on, but they can still respect the choice you’ve made. You and your team don’t always have to agree, but you should be aligned on what’s best for the business. 

“People need context behind why they’re doing things. I have had situations where a decision has seemed baffling to me, but once I learned the reasoning behind it, it totally changed my perspective. Explaining our thought-processes when we make decisions or implement new things helps the team be aligned in a common goal and it has made a huge difference, even if they don’t necessarily agree with the initial decision.” 

– Kristie Holden, VP of Marketing

You will give bad advice

You don’t expect other people to know everything, but it’s easy to fall down the trap of expecting that out of yourself, especially when you’re a small business owner. Since you’re only human, eventually, you will lead your team down the wrong path with bad advice. Whether it’s advice that’s irrelevant to a new situation, something you read in a leadership book, or just an idea that sounded good at the time, at some point, you’re going to give the wrong answer. 

To recover: Slow down! Accept that it’s okay to not always have the answer. You will gain more respect when you let someone know you’ll need to look into something and get back to them rather than aiming to appear informed even when you’re not. Take a step back to gain perspective and logically diagnose the problem or concern. Always stay curious – remember to ask questions and, much more importantly, listen. 

“As a business owner, you’re in a position where people expect you to know the answer or you feel pressured to have an answer. But if you can accept that it’s okay to not know, then you give yourself space to think, ask, or just say “I don’t know” and then either go research or ask someone else. I’ve struggled with this one because I tend to make decisions fast, then think about it later and change my mind. So I’ve had to learn to think through my decisions out loud. If I’m unsure or need someone else’s input, this helps others have time to think it through and then we can decide on something together that makes sense.” 

– Kristie Holden, VP of Marketing

You will pursue the wrong strategy

As your business grows, the stakes get higher. Decisions get harder to make and the risk of making the wrong decision is greater. At some point, you’ll make the wrong decision, choose the wrong strategy, or just fail at executing the way you should have. Sometimes, you may even do everything right following a strategy that works for another business, but not your own.

To recover: Learn from your mistakes. After you’ve recovered from a strategy or method that failed, ask yourself and your team what went wrong. Start to build trust in your team and your own judgment by analyzing your actions so you know what will work in the future. As you see mistakes happening, move fast to shift as soon as you’ve realized you made the wrong decision and make sure to set the expectation that your team can always speak up if they notice something that can be improved. 

“It helps to get in the habit of questioning if things are working and if there’s something you should stop doing or change. To build this habit we do Monthly Retros. What was supposed to happen? What went well? What didn’t go well? What did we learn? This builds the culture of challenging and adjusting so you’re not stuck in decisions. It creates space for questioning if you’re on the right path and if a decision is leading you down the path with the right outcome or not. By having this culture everyone feels comfortable challenging and questioning decisions so you can correct sooner and learn from mistakes. This is Kaizen! We also document our learnings each quarter and review them before planning the next quarter. This way we’re taking lessons learned with us so we can be deliberate about not making the same mistakes.” 

– Kristie Holden, VP of Marketing

Bonus: You can’t avoid mistakes. Don’t try.

When it comes down to it, no matter what your role, you’re going to make mistakes. Don’t waste valuable energy on trying to avoid them. Instead, work with your team to build the resilience it takes to recover from these mistakes. Spend time on postmortems after your projects to understand what you did well and what went wrong – and take everyone’s feedback. Focus on being able to recognize problems and bottlenecks as they’re happening so you can quickly shift to recovery mode. Stay focused on what you want to accomplish, put your team first, and have the willingness to experiment and learn from mistakes. Most importantly, you may have noticed a trend in all of these tips about leaving your ego at the door. If you want to be a good leader, you need to give yourself the opportunity to learn, improve, and you must humble yourself to take constructive criticism well and often. The more self-aware you are of your own shortcomings, the stronger of a leader will you become.  

Daylite Tip: Use Daylite Forms for your postmortems so you and your team can learn from mistakes and track your improvements over time.  

About the author:
Kristie Holden is the former VP of Marketing at Marketcircle/Daylite. She’s now an online marketing consultant. She helps startups get more leads by clarifying their message and creating a marketing strategy to attract and convert their ideal client. Connect with her on Instagram.

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