Five job mistakes anyone early in their career can learn from

Dan Richards is a serial founder and former public company chief executive officer, and an award-winning member of the marketing faculty at the Rotman School of Management, where he oversees the credit course associated with MBA student internships.

Each year, 250 Rotman MBA students complete a 13-week internship that’s required to graduate. Afterward, students submit an assessment of what they learned and write a letter to their younger selves with advice on how to make the most of the experience they’re about to begin. In this letter students talk about what they did right as well as the mistakes they made and what they wish they’d done differently.

Five themes emerge from these retrospective assessments. These themes are then framed as imperatives for success so that students starting internships can learn from the mistakes that previous students made. I also share these lessons with graduating students taking on full-time roles – the lessons from student internships apply to most employees early in their careers.

Imperative 1: Adapt to work norms

Working hard isn’t enough – new hires have to work smart as well. The key to doing that is understanding the manager’s expectations and the norms for the workplace.

At Rotman, internals ask managers to provide short, written feedback after four weeks. That feedback will sometimes have comments like, “This student is hugely capable but needs to understand that when we ask for a report, we’re looking for two pages, not 20.” Another comment last summer: “For a 30-minute presentation, rather than circulating findings before hand, this student tried to cover them in 40 slides and there was no time for questions, which is where we see the most value.” When you’re new to a role, job No. 1 is understanding the expectations. Asking for a previous report or presentation to use as a model can be key to ensuring you deliver what’s expected.

Imperative 2: Ask clarifying questions

One of the most common regrets from students is failing to ask questions early in their internship. Whether asking for the meaning of jargon or getting guidance on how to respond to a client request, questions can help new employees avoid pitfalls that will send them down the wrong track and waste time.

Sometimes students worry that asking questions will raise questions about their competence. But almost always the problem isn’t asking too many questions, it’s not asking enough. In Rotman’s orientation session for students heading into internships, we point to data on how we underestimate the desire of most people to be helpful. We also discuss research that when you ask someone for advice, as long as the issue is meaningful and you aren’t asking all the time, rather than eroding people’s impression of you, asking for advice can enhance the way you’re viewed.

Imperative 3: Demonstrate initiatives

How do you stand out when you only have a few weeks to show your value? If all you do is the job you’re given, getting noticed will be a challenge. One student wrote, “I did the work I was given but only realized too late that I should have shown initiative to go beyond this.”

The winning mindset is to do the task you’re assigned and then think about how else to contribute. One student initiated a survey of work-from-home attitudes that she was asked to present to the senior team. Another colleague asked about the glitches that stood in the way of their productivity, presented these findings and got approval to translate into process improvements. A third received permission to form a working group of interns to recommend improvements on how the next cohort of interns could be on board. However you do it, going above what’s expected is something almost every manager looks for and welcomes.

Imperative 4: Speak up in meetings

Some people struggle to speak up in meetings. Last summer one manager wrote, “I know this student has great ideas because she shares them with me one on one, but she needs to express her views in larger groups.”

One student wrote, “I knew that I should speak at meetings but couldn’t bring myself to do it.” This is surprisingly common – Warren Buffett talks about his difficulty speaking up until he takes a public speaking course. That course was pivotal to his success – as a result, hanging on the wall of his office is not his MBA degree from Columbia, but the certificate of completion from this public speaking course. Rotman offers optional Speaking with Confidence sessions where students meet weekly in small groups to build confidence. Whatever route you take, getting past the hesitation to speak up can be the key to success on the job.

Imperative 5: Invest in relationships

If you want to get noticed and advance, most of the time quality work is only one component of the answer. The other part is that your manager and colleagues enjoy working with you and want you on their team.

In most workplaces, doing that means making the effort to develop informal relationships. It means observing how co-workers socialize and taking advantage of invitations to join colleagues for coffee or lunch. It can also mean accepting an invitation to participate in an after-work soccer match or softball game.

And sometimes it requires students to get out of their comfort zones and make small talk or ask colleagues about their weekends. It’s important not to force this – to be effective, this has to flow naturally. New employees need to make building relationships a priority. One student talked about the regrets of turning down an invitation to join a colleague for lunch because he wanted to double-check his work. Checking his work could have waited – and the invitation never came again.

For both interns and graduating students starting full-time roles, at Rotman, one of our messages to students starting a new role is to take control of their experience. Ultimately, adopting a mindset where they first seek to understand and then act on the imperatives for success in their job will tilt the odds of a positive outcome in their favour.

This column is part of the Globe Careers’ Leadership Lab series, where executives and experts share their views and advice about the world of work. Find all Leadership Lab stories at and guidelines for how to contribute to the column here.