In honor of the season of giving thanks, I want to take a moment to look back at my past year with Skaled. It was a mix of uplifting triumphs and frustrating fails, but culminated in three major lessons learned that I’m so thankful Skaled has helped me cultivate.

 1. It is very RARELY an emergency. Do not panic.

 Before entering the startup world, I worked in book publishing. My entire work experience was with two massive organizations focused on details, details, details. These tiny pieces of huge puzzles were often made to seem earth shattering. It was not uncommon to see an assistant with a piece of paper clutched in hand, sprinting towards a meeting with something “urgent”. Whether this was merely my perception or the norm amongst working bookworms is up for debate, but this was the mindset I brought with me when I joined Skaled.

This type of panicky energy is devastating to a small office environment.

When I was stressed and antsy, my mood rippled directly to Jake, my CEO.  In those days it was just us – crammed into a client’s office. I quickly learned that my mental calm was essential to keeping our work environment productive. This skill has since translated directly to my sales. Remaining composed under pressure when a prospect objects on a big deal makes or breaks my ability to close. Being able to control my tone and articulate with the right amount of urgency, rather than panic, is crucial.

 2. Know when to hold ‘em.

Kenny Rogers said it best. “You got to know when to hold ‘em, know when to fold ‘em”.  One of the most exciting and terrifying aspects of a startup is that there are often questions without answers. There’s a lot of building the plane as you fly it, and constant iterations and pivots that happen mid flight. Picking your battles becomes very important. You don’t want to be the incessant squeaky wheel, but you also don’t want to allow mistakes to happen without correction.

 By raising your hand the right amount, you can challenge given solutions. That is what makes this ecosystem so much fun to work in. But it’s important to know when this is appropriate, and how to deliver your suggestions. I have come to love the days when I get to say, “No, wait a minute – I disagree.” Productive debate is encouraged in the startup world, and at Skaled, it has helped foster a culture of teamwork and participation.

3.  Saying “no” is just as important as saying “yes”.

I am inherently a people pleaser. While this quality has positive traits, it can also be one of the most deadly, when working in sales. Over promising to close a sale will likely end in a bad deal, rather than creating a strong relationship. To avoid this, I’ve learned to assess my allegiances and prioritize accordingly.

For example, when selling for a client, first and foremost my job is to make sales for that client. This also encompasses walking the tightrope between offering incentives, and still maintaining the integrity of the offer. I am still improving on this skill, but understanding how to navigate this situation has been a really valuable revelation.

Irwin O'Donnell