Tag Archives: startup

6 Leadership Mistakes To Avoid

20th Century Fox/Office Space

20th Century Fox/Office Space

I founded my first company in 1998 and my second in 2013. I’ve worked with hundreds of companies as clients in my career – from startups and small businesses to large, enterprises – and have managed employees from coast to coast. So, I’ve seen a lot in regards to leadership, HR and management. I’m not perfect – I believe the best leaders are always learning, just like everyone else – but here are six mistakes I’ve seen leaders repeatedly make.

  1. Micro Managing – Especially at the C-level, leaders should have confidence to let the people they hired do their job (which often includes managing a team of their own). Hold employees accountable with specific goals and metrics – if they don’t meet them, figure out why, together. But if you have to micro manage your team (see their To Do list every day, ask the same questions over and over, etc.), you’ve either hired the wrong people or you’re not focused on the bigger picture.
  2. Being Too Hands-Off – it might seem contradictory to point #1, but you can’t disappear as a leader, either. There’s a difference between paying attention and ensuring everyone is meeting goals, vs stepping away and never checking in on progress towards those goals. It’s not good leadership form to ask, “Is it done?” the day something is due.
  3. Worrying About Everyone’s Feelings. On one hand, you need to lead in a positive manner. On the other hand, this is business. You can’t keep everyone happy, nor should you try. Avoiding conflict or tough decisions due to fear of hurting someone’s feelings is a good way to lead in the wrong direction.
  4. Failure to Dig Into Data. What’s working and what isn’t? If you know, great. But do you take it the next step to find out why something is working or isn’t? With all the data available in business today, smart leaders understand to dig in and analyze it both when things are great – and when they’re not so great. This allows you to repeat winning formulas, and understand the downfalls of your organization so that you can lead to improvement. This includes staff, resources, money, ideas – and all the combinations therein. (And don’t be naive enough to think you’re an organization with no downfalls.)
  5. Wasting Money.  I particularly see this in startups. Especially after said startups close funding. Although, I’ve also seen plenty of it in large enterprises where checks and balances get more difficult to track through multiple layers of spending. It’s always surprised me how many startup CEOs, specifically, don’ t really track where the money goes, and if the spending is wise in relation to where the company is in its lifecycle. It’s easy to get caught up in the visceral items – marketing, events, sponsorships, branding – cool business cards, hiring a big name PR firm, or sponsoring a popular tech publications’ startup event. These are all things I’ve seen (especially first time) founders get excited about because it brings cache and (temporary) attention, and makes things feel “real.” But are those the items that are going to close customers for your early on? Are they helping you to develop a better product? There’s a difference – a big one – between what a startup should be spending on vs a decade-old company with a solid customer base and revenue stream. Good leaders shoot down the more “fun” ideas in the early stages, and keep their teams focused on what’s going to bring in the right elements to the company – and continue to apply that insight during each of its lifecycle and growth stages.
  6. Bad Communication And Failure To Listen. It’s absolutely mind boggling how bad leaders can slow down the progress of a company simply by not listening. They don’t take notes in meetings, don’t record or remember outcomes, interrupt often, and forget what they’ve assigned to, or asked of, people. This results in employees, partners and even vendors having to repeat work, waste time explaining what they’re working on – for the 3rd time this week – and everyone feeling frustrated and misunderstood. Leaders listen. Leaders record. Leaders remember and leaders communicate clearly. Too many leaders think they don’t need to communicate clearly because everyone should just know what they want. This doesn’t work in personal relationships, and it doesn’t work between employer/employee relationships, either. Be clear, be concise, be consistent.

What mistakes have you seen by leaders, and how did it affect you or the company in the long run?


Thinking of Turning That Hobby Into a Small Business? 3 “Can’t Ignore” Things To Consider

When we’re young, it seems we are asked very early on what we want to be when we grow up. I was never married to just one image of my adult self – as most kids aren’t at a young age. We want to be a lot of things – dancer, doctor, vet, Olympic champion, lawyer, horse trainer – the list goes on and on. Yet as we grow up, we are expected to choose just one thing and stick with it. We study it in college or train for it as an apprentice. We toil away to an entry level job in our chosen profession so we can spend years climbing the ladder. Once we get up there, sometimes we stop and remember all those other cool things we wanted to try, often turning them into hobbies that we find play around with from time to time.

But what if you want to reignite your love for something and pursue that dream after all? You find yourself pulled in the entrepreneurial direction to turn your hobby – jewelry design, singing and songwriting, hairdressing, photography, or whatever your passion is – into a business. You’ve found people are interested enough in what you have to offer, and you believe you can make a living this way – so now what?

I can speak from experience that creating a successful business takes a lot more than love for your hobby. You’ll find yourself wearing many hats and you’ve got to prepare to fulfill multiple roles and responsibilities in making the business a success. While you can always hire experts as you grow, be prepared in the early years to think about – and manage – these other elements as well.


Although many people feel they are smart enough about their core audience to execute marketing and PR on their own – after all, who knows your story better than you do – they forget the time and resources it takes to do marketing well. How will you develop content that breaks through the noise? Where will you put it – online or off? How will you manage interactions and engagements? Will you have time to maximize your marketing investments to ensure ROI?

As a solo or even partner act, it will be crucial to clearly identify who you want to sell to (who do you believe is going to buy – not just admire – your work?) and choose a few select ways to market intelligently. This includes identifying a strategy to fit your budget and to scale with your ability to meet the needs of any incoming business as a result. The good news is that there are a lot of marketing consultants out there. The bad news is that you have to filter through the myriad of self-proclaimed experts to find the best fit. Don’t just hire someone based on what they say, but on their reputation – because you’re putting your reputation in their hands as well. Check references, ask for case studies and do some easy preliminary online searches. Any great marketer today will have a strong and credible online presence. And that doesn’t just mean numbers of connections – it means having quality connections with influencers, so be sure you’re looking through who they engage with, are linked to or followed by in social networks.


Ah, the government. There’s a lot to know about owning a business, including state and federal tax filing requirements, personal risk and liability of each type of business (S Corp, LLC? Etc.), rules around hiring contractors vs full time employees and more. Make sure you invest in a great accountant and if possible, a good business and legal advisor who can help make sure you understand and adhere to the ever-changing laws. In addition, each state is different, as are cities. Sometimes, for example, if you’re selling good or services in a state outside of where your business is based, you can be required to pay taxes for the privilege of doing business in that city or state – or both.

In addition, you’ll want help with someone who can crank out appropriate contracts, manage vendor or customers requirements and more. It’s easy to get overwhelmed with the myriad of legal requirements in running a business – but they can’t be ignored. So get some good help. Ask other small business owners in your area who they’ve worked with, and ensure you ask for references. Too often, legal counsel takes control and you end up feeling like you work for them. Remember, it’s the opposite – you’re paying them – so find someone smart, assertive and trustworthy that has you and your business’ best interests at heart. And that includes understanding your financial abilities, and working with you in a manner consistent with such.


Time after time, I sit down with business owners, leaders and operators, and HR is always one of the biggest headaches listed. It’s complicated – because people are complicated. But it’s impossible to grow a company without growing staff, so it’s inevitable that managing HR will become a good chunk of how you spend your time. It’s certainly complex enough to be job all on its own – but it isn’t what you set out to do with your life, so get help. From time-intensive recruiting and hiring to emotionally- and sometimes legally-complicated management, I recommend doing your homework and finding an expert (or two) from the get go. This will enable you to focus on your core business, and can often help you to have a better relationship with the people you work with because there’s a conduit to handle tough conversations, keep up with legal requirements and handle the mountains of paperwork involved.

Whether you’re just thinking about starting your own business, or are in the throes of planning and execution, thinking about these core areas will help you get started off on the right foot. I also recommend following small business experts and entities on social networks like Twitter, and reading through the U.S. Small Business Administration website.

Boston Entrepreneurs #Unpitch VCs

Securing funding for your startup can be both daunting and difficult. The plethora of crowdfunding companies and those claiming to connect you with VCs – for a price – don’t make the landscape any easier to navigate.

A few folks in Boston are collaborating with New England Venture Capital Association in hopes of making the process easier for startup entrepreneurs, via December 11’s first “Unpitch.” A free event, #unpitch is “a new event geared to entrepreneurs interested in connecting with investors.”

I can vouch that there are some pretty credible names involved in this endeavor, from both the organizational side, as well as the VC side. So why not take your chance and “unpitch” your business? Caveats are that you need to be willing to talk openly about your idea – not just to VCs but in front of the other chosen entrepreneurs. Game? Here’s how to apply. (Deadline December 1). Good luck!