Don’t skip “How can I help?”

Counselors and parents, if a student presents you with a challenge or a situation they’re facing where they don’t know what to do, it’s tempting to jump in and offer solutions.

“I want to take AP Chem and orchestra, but they’re offered in the same period.”

“My parents want me to apply to their alma mater, but I don’t want to go there.”

“I didn’t make the volleyball team and there are no other activities that interest me.”

You (think) you know the answer. You’re ready to dish out the advice it seems they desperately need. But before you solve their problem, take a minute to understand what they think the problem is. Ask questions. Get more detail. Gently get to the heart of what they’re thinking, feeling, and facing.

And once you’ve got a clear sense of that, then ask, “How can I help?”

Now, here’s the key. You don’t necessarily need to agree to whatever they request. If your student says, “I want you to call the counselor and demand that they rearrange the school schedule so I can take both classes this semester,” that’s likely not a request you’ll want to honor.

But there’s a subtle art behind this question: it makes the asker take ownership. They need to think through the issue, assess where they need help, and then ask (or not ask) for it.

You’re not jumping in uninvited. You’re not preemptively solving a problem you weren’t asked to solve. You’re not removing the opportunity for them to learn, to spot their own solutions, or to assess what kind of help they need or don’t need.

You’re just asking, “How can I help?”

The question is important. Don’t skip it.

A token apology with the right token

Regular readers know that I’m a fan—and a customer—of the company Basecamp. In November, their software went down for the longest period of downtime in company history. And in this episode of their podcast (you can access other ways to listen at the podcast’s main site), their CTO, David Heinemeier Hansson, details how they responded, communicated with, and ultimately apologized to their customers.

Hansson points out that when you let a customer down, you have two tokens available to you: 1) This is a huge deal, and 2) This isn’t that big of a deal. When you grab the first token, the odds increase substantially that the customer will grab the second token.

Basecamp has hundreds of thousands of paying customers. When the software was down for an entire day, only one customer expressed outright anger (turns out they were in fact deeply affected). And many others wrote in expressing their support, understanding, and devotion to the product.

You don’t have to be in business to use this approach. The next time you let someone down, take the right token and see what happens.

Open the door, or close it?

In the last 10 days, we’ve received over 300 applications for open positions we’re currently recruiting for at Collegewise. With that many applications, we have to turn away a lot more people than we can hire or even interview. And we think applicants who show an interest in us deserve to be treated with respect, especially if they really take the time to put together a thoughtful cover letter to help us get to know them. Applying for jobs can be a demoralizing experience for even the most intrepid job-seeker, and it’s important to remember that there’s always a person behind the paper.

Still, it’s interesting to see how some people respond to an email telling them we will not be offering them a position. Many reply and thank us for the update, citing how many jobs they’ve applied for and never heard anything back. Some express their disappointment and understanding, along with a sincere desire to be considered again if the right opportunity were to arise. And some tell us what a mistake we’re making. One applicant last spring responded to a personal email explaining why he wasn’t selected with only, “Whatever man. Your loss.”

When someone responds like that, what are they hoping will happen?

I’m not suggesting they’re a bad person or even that they’re wrong. Maybe we are making a mistake. Maybe we should have offered them a position. Hiring is an imperfect science and even the best process can’t guarantee you’ll get every decision right.

But a reply like that shuts the door. The conversation is over. What reason do we have to come back to them in the future, or to pass along a referral for another opportunity, or reach out and reconnect at a conference? We’re not holding grudges, we’re just taking the signal that this person is done with us. If that’s the intention of the reply, message received.

There’s no right or wrong here, and I don’t expect anyone to pat us on the back after we say no. But everyone deserves to find a job where they can be happy and successful, and it’s important to be intentional about which doors you close, and which you leave open.

Private counselors, how do you respond when a family chooses a competitor over you?

Students, how do you respond when you aren’t selected for a team, class or leadership position?

Colleges, what do you say to the student who informs you they’ve accepted another school’s offer of admission?

Your response to a no has an effect, one that can either close the door or keep it open. Before you respond to a no, decide what you’d like to happen with the door.


The relaxed roommate strategy

My college community was one in which everyone moved at least twice a year. Whether you lived in a dorm, an apartment, or a rented house, the majority of leases lasted from September to June, at which point you’d have to locate summer housing only to move yet again in the fall to start the cycle again. My roommate Sean got so tired of it that he completely abandoned any semblance of packing for a move and just threw all of his belongings in garbage bags while chanting the mantra, “Get in and get out, Kev!”

For some of us, impending moves were a recurring source of stress. Months before you reserved your U-Haul, you had to align yourself with future roommates, agree on a budget, search for a residence, and lock everything down lest you were left to live in your car or to move home. I’ll admit that I was in the stressed camp. I spent just as much time worrying about housing as I did actually looking for it.

But other students never seemed to worry about it too much. They didn’t wrangle roommates. They didn’t search for houses. They didn’t imagine all the worst-case scenarios that hadn’t actually happened yet. They’d just settle into a Zen-like comfort, somehow assured that everything would work out OK.

And magically, they always found a place to live.

Yes, those relaxed kids didn’t always end up in the perfect scenario, but neither did the relentless planners. And while the easy-going campers often benefitted from the work of those of us in the stressed camp, they were just as frequently the saviors, the ones who still were uncommitted when someone else desperately needed another roommate.

I wouldn’t suggest that any student sit back and wait for other people to handle your college planning for you. It’s your future and it deserves to reside in your hands. But worrying is rarely a useful strategy, whether or not you’re a planner.

For those of you worrying about every potential outcome that hasn’t happened, obsessing over elements that are not in your control, injecting anxiety into areas of your life to such a degree that it permeates the otherwise restful or fun time you should be enjoying, maybe you could take a page out of the relaxed roommate’s book?

Planning might change the outcome, but worrying almost never does.

Tardiness vs. timeliness

We like to be on time at Collegewise. It’s something we expect from our colleagues, our students, and ourselves. We even talk about it in the “Culture, values, and unwritten rules” section of our employee handbook:

“Timeliness is Wise. Be on time. To everything. Don’t leave a family waiting in your office or on a Skype appointment because there was “so much traffic.” Don’t roll in five minutes late to a meeting with your team because the line at the coffee shop was too long. If you struggle with punctuality, here’s a system: (1) consider what you would do if there were a million-dollar cash prize at stake based on your on-time arrival; (2) whatever you answered for #1, do that.”

When you’re late, there are multiple prices paid. You’re paying with your reputation, and whoever is left waiting is paying with their time. Not everything has or needs a hard start time in life or at Collegewise. If someone throws a barbecue and says, “Come over around noon,” no reasonable person expects you to be knocking on the door at 11:59. But it’s not hard to tell the difference between a time that’s intentionally soft and a specific time that’s a mutual agreement in principle. If the message you send to the world is that you’re chronically late, the world will respond accordingly and decide you’re not as reliable as you could be.

I really enjoyed Seth Godin’s recent post, “Good intentions (how to be on time),” because he not only gives late-comers the benefit of the doubt by assuming they don’t actually want to be late, but he also helps them think about the factors leading to their tardiness and offers some steps to address the problem.


It’s hard to imagine a group, team, or project that doesn’t benefit from a self-starter, someone who sees an opportunity and then steps up.

  • What needs to get done?
  • What’s broken and needs to be fixed?
  • What could be improved and made even better?
  • What opportunities are waiting?

Self-starting doesn’t always mean you have to do it by yourself. But starting, whether it’s the idea or the action, almost always starts with one person. And you don’t need a leadership position, authority, or an invitation. You just need yourself and the willingness to start.

Imagine how your future college application might change with a little more self-starting.

Where are you at your strongest?

Last month, I was chatting with Michael, a Collegewise counselor, about the difference between introverts and extroverts. I suggested that the easiest way to tell which of those camps a person belongs in might be to ask them how they feel when they walk into a gathering like a party where they don’t know a single person.

His face lit up and he replied, “Oh, that’s my favorite thing in the world to do!”

Faced with the same situation, I can circulate, make introductions, and from all appearances look like I’m enjoying myself. But it is far from my favorite thing in the world to do. In fact, it exhausts me. One hour of small talk takes the mental toll that a one-hour run takes on me physically. I need downtime to recuperate afterwards.

Marcus Buckingham, the author of Now, Discover Your Strengths, pioneered the Gallup Organization’s approach to leverage a person’s strengths as opposed to fixing their weaknesses. And this short video shares his three recommendations for success in your career, all of which apply to high school students hoping to succeed as college applicants.

This tidbit in particular stood out to me.

“Your strengths are not what you’re good at, and your weaknesses are not what you’re bad at. If you’re good at something, but it drains you, that’s not a strength, that’s a weakness. A strength is an activity that makes you feel strong, just as a weakness is an activity that makes you feel weak. A strength draws you in, and you know better than anyone else what your strengths are. And if you don’t, then it’s time to learn.”

As you think about where to put your efforts this year, please make sure you prioritize maximizing your strengths over fixing your weaknesses (strengths improve more than weaknesses do). And you might start that focus by asking not, “What am I good at?” but rather, “What makes me feel strong?”

Successes to show for it

Last week, I sent out an invitation to every full-time employee at Collegewise to participate in an experiment: The Talent Tour of Duty. Our Talent Department is responsible for finding new Wisers to join us, for onboarding and training them, and for helping everyone at Collegewise be successful and engaged. The Tour of Duty is an 8-week stint for coworkers who want to help us do an even better job in those areas. It’s like an internship, but not the kind where you do mindless labor that later masquerades as “experience” on a resume. We want it to offer work that challenges participants and makes them proud to put their team’s name on it when it ships out the door.

But it might not work.

What if nobody applies? What if they don’t enjoy the experience? What if it doesn’t make the changes we’re hoping for? All of those things are potential outcomes. It’s an experiment! We can plan and execute with the best of intentions. But like everything from prom proposals to sports strategies to investment approaches, all the diligent planning and best intentions can’t insulate you from failure. The only way to do that is to engage only in those projects with guaranteed success. And those almost never allow for innovation, creativity, or fun.

So we’re taking the risk. And we’re OK with that.

You can’t enjoy success without some failure along the way. Sure, if this project fell apart because we just ignored the work and the people, that’s an ugly failure. But if all the best intentions and follow-through don’t lead us to the outcome we’d hoped for, then we’ll learn what we can and move on to the next experiment. If we can rack up enough of those original projects this year, we’ll inevitably have some successes to show for it.

Saying goodbye to a leadership giant

Herb Kelleher, the founder and past CEO of Southwest Airlines, passed away this week at 87. I was 22 and in my first job out of college when I became aware of him via the book Nuts!: Southwest Airlines’ Crazy Recipe for Business and Personal Success. His approach to business—stand for something, treat your employees well, mix work with healthy doses of joy and fun—reminded me of my boss at the time, Paul Kanarek at The Princeton Review, who I’m proud to say is now my business partner at Collegewise. And it was one of the first times I imagined what I might want a company to look like if I ever started my own one day.

Herb Kelleher had a vision for a company and a service that did not yet exist. He made that vision a reality that was successful by most objective measures (Southwest is the only airline to have 46 straight years of profitability). And he staked that vision on a set of principles from which he never wavered. I wouldn’t recommend that anyone try to mimic Herb’s personality because you’ll never out-Herb Herb. But the way he approached his work and his relationships with coworkers is an illustration of leadership that any student, parent, counselor, or Collegewiser can learn from.

If you’re interested, here’s a good primer of Herb’s work, leadership, and legacy.

How to get your resolutions right

If you’re making New Year’s resolutions this year, here are a few links I’ve shared in the past, plus a new addition, to help you make and keep resolutions that work for you.

Chip and Dean Heath (who teach at Stanford and Duke respectively) offer “4 Research-Backed Tips for Sticking to Your New Years Resolutions.”

Here’s author Dan Pink on the science of behavioral economics as applied to New Year’s resolutions.

30-minute podcast on the Freakonomics blog about why willpower alone is not enough (and what to do instead).

And finally, a New York Times piece, “The Only Way to Keep your Resolutions.”

Happy New Year, and thanks for reading.