Why Your Boss Wants to Hear “Let Me Try”

Your first 90 days at a new job are perhaps your most important in the length of your career.

Many companies will hire you on contract for that time – think of it as a “make or break” trial period to see if you have what it takes. It can determine the length of your career at that company, the expectations your managers have of you and even how high you rise.

As I’ve watched my team grow, I’ve seen how differently folks encounter their first 90 days at Kiip. Some have shone brighter. Below are a few tips on what to do in your first 90 days.

How to navigate your first 90 days at a new job.

Image source: Flickr, user: Sergio Alvarez

Set your own goals, even if it’s not the norm.

It can be tempting when you’re in your initial training period to let your manager decide your goals. However, that won’t win you any favors.

It’s important to set your own 30-60-90 day plan for what you want to accomplish and learn on the job. Communicate the goals proactively to your manager. Even if you’re at a big corporation where much of your work is pre-determined, you can still choose a project to focus on after your daily tasks. It lets you set your own tempo in the best way possible.

Since I always see being a manager as being your enabler, you can expect that a good manager will help you achieve those goals in the best way that they can. At Kiip, it is crucial that we make sure people have the right structure and resources to achieve goals as efficiently possible.

Say yes to everything.

Many founders use the “startup” excuse to push insane hours, making it tough for employees to find work-life balance. But during your first few months, resist the urge to leave when the clock strikes five.

Early on, there are a lot of opportunities to observe and help with projects outside your daily scope. Instead of checking out, ask your manager if there’s anything else you can assist with before you leave. Even if it costs you a few extra hours, say “yes” or “let me try” to every opportunity that lands on your plate, unless you absolutely know it’s something you can’t do. Showing initiative in the beginning pays off. Once you’re settled and looking for a little more “you” time, you can prioritize and delegate without looking lazy.

Make sure the CEO knows your name.

Reporting to your immediate manager(s) doesn’t mean you’re limited to only interacting with them. At any point in your first month, schedule an informal coffee meeting with your CEO – or the head of your department, if in a larger environment. You’d be surprised how much they really care about your success. It’s important for them to understand the fresh perspectives brought to each team, so newcomers have a unique chance to make suggestions on upcoming projects. The excuse of “being new” gets you a lot of leeway.

I try my best to meet everyone who requests a one-on-one, even if brief. This can be a walk to grab a coffee or a quick meet and greet. I like to make sure that everyone knows they have direct communication channels to the executive team. This is crucial for startup culture success.

Say hi to everyone (in your own style).

In the first couple weeks, say hi to everyone around the office. A nice smile, a firm shake or a quick note about how excited you are to join the team makes an impact.

Introverted team members may become more reserved if they don’t get a chance to open up early. Creating this openness with a first impression ensures that co-workers have met you and understand your role. Of course everyone has their own personality and style, so do it your own way!

Set your own reviews.

In a startup environment with less structure, feedback doesn’t always come to those who wait. It was true when we first began Kiip and it taught me a lot about how to position management.

Since you already set your own goals, schedule a review between you and your immediate manager after three months. Give your manager at least a day’s notice and tell them what you want to discuss: your current responsibilities, an expansion of your role, a project on the horizons and so on. Read out the key performance indicators (KPIs) from the 30-60-90 day plan that you set when you started and boast about the progress you’ve made. You’ll define your own success and give visibility to your recent projects.

While some may find it hard to brag about their accomplishments, it’s necessary to shed light on your hard work. Personally, this is how I’ve learned about my more proactive employees and how they made big differences within our company.

Understand subtle power dynamics.

Especially in startups, where most employees choose their own titles and wear a dozen different hats, it can be difficult to understand the office hierarchy. Is Jane in Marketing your peer or your superior? What about Bob in Sales?

Mentally note where your colleagues stand to determine who holds more power and who can alleviate any bottlenecks. But remember to be open-minded about hierarchy. Sometimes titles mean different things at startups; they may hold more or less weight depending on the overall flatness of the culture.


Kiip redefines how brands connect with consumers through moment-based rewards in everyday apps. As part of our innovation strategy, we’re motivated by challenges, curiosity and a love for learning.

We’re looking for talented employees to join our team! Visit kiip.me/careers to learn more.

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  • Avinash

    Excellent insight!!!

    • brittanyfleit

      We’re glad you enjoyed. Thanks for reading!