Tough love: Oxymoron or perfect match?

Here’s my story about why I think a little tough love can change lives, in a big way and forever

I’m the oldest of five kids (four daughters and one amazingly tolerant and resilient son) and there’s nothing that makes me happier or feel luckier than being with my siblings. For our family’s annual summer vacation this year, I had the chance to hang out with them at the beach and do a whole lot of nothing with all of them, along with their spouses and kids.  

My youngest sister/sibling—who is twelve years my junior (and was once accused of being my son when I was 13 and she was a baby)—is now the closest thing I have to a doppelgänger and about to turn the big 4-0. An Austin-based lawyer who’s now taking a break to raise her three kids who are all under ten, she’s been incredibly supportive of this whole Women@Work endeavor and always full of ideas for new and better things we can do to help professionals at all phases of their careers. I’m so grateful to her for so many reasons. (Thanks, Mo! ☺) 

Anyway, during one of our many awesome hang-out-and-do-nothing sessions this past week, she said to me, "You need to do a post on the importance of tough love and the life-changing impact it can have on someone who needs it.” She suggested it because of a particularly tough but loving session I imposed on her just after she graduated from college and moved to Boston for the summer. Although she was one of the smartest people I knew/know and had everything going for her (then and now), she was the picture of everything but those things at that point in her life. Overweight, disheveled appearance, poor posture, a shuffle-ish walk, a presence that broadcasted insecurity, and just an overall "Debbie Downer” personality that blamed others for all sorts of things, she had devolved into something that: 1) wasn’t who she was or could be and 2) didn’t align with what she wanted to accomplish. 

I took her to lunch at a cool gastro-pub, ordered us a couple of beers, and said, "This is tough for me to say and will probably be more difficult for you to hear—but you need to get yourself together. You’re crazy smart and funny and talented and educated and have everything you need to be successful. However, you’ve lost your way somehow. If you applied for a job and interviewed with me, I would not hire you at this point—even though you went to a great school, got good grades, and have a bunch of other experiences that would make you a good employee.

"You need to change the way you’re coming across if you’re going to get the job you want and have people engage with you in a way that will feel positive and realize success for you. To achieve that, you need to address your whole external appearance and persona.” Then I told her the next time she looks in a mirror, she needs to ask herself the following questions: 

  1. Do I look like someone I would want to spend time with, who seems fun and interesting and would get along with other people? Am I someone who looks like they’d have a good attitude every day and be up for anything, taking on new people, places, and things with a "hey, I can do this!” and “how can I help?” attitude?

  2. Am I someone I would trust to do a good job and see things through in a high-quality way? Am I someone others would want to invite to lunch or want to have in the room helping them to solve problems and get things done?

  3. Am I someone who would represent "the company” well—both internally and externally with customers and other stakeholders? Am I someone who would embody the brand of the company and what they’re trying to achieve?

And here’s where the tough love really came into play. I said, "To achieve this, you really need to lose weight and get yourself into shape. You need to buy new clothes and clean up your appearance. You need to do something about your hair. You need to ensure that everything about your physical appearance conveys a picture of who and what someone would want to hire. You need to pull together a kickass resume and find a job, any job, just to get moving on some sort of career path. This might all sound superficial, but it’s human nature to evaluate people, places, and things based on the way they look and consider that as a key factor along with everything else on your resume, what you say, and what others say about you. Without addressing all of these things, you will continue to be miserable and think it’s everyone else’s fault instead of looking in the mirror and taking responsibility for making yourself: 1) happy and 2) successful.”

I then turned to focusing on the how: "All of this might seem overwhelming, but I know you can break all of these individual things down and address them one by one. You need to start immediately or else risk entering a death spiral through your 20s that will be nearly impossible to overcome and you won’t know why. You’ll end up bitter and frustrated and sad and angry and not where you want to be or who you want to be. All that said, I want to reiterate that you’re absolutely amazing, have all the raw ingredients to get back on track, all of these things are imminently doable for you, and I’m willing to help you do any or all of it.”

Fast-forward nearly two decades and her comments of gratitude at the beach last week really warmed my heart (just as they have the 10+ times she’s thanked me in a similar way over the years for this one seminal tough love session). To be honest, I was very worried going into that conversation 18 years ago that I might exacerbate her problem(s), making her feel worse about herself and her situation. I knew there was a chance it could go either way—jolting her into a new era of self-improvement and living her best life or sending her into a further pit of self-despair and feeling overwhelmed with failure. Luckily for both of us, she nodded her head and said, "I know…you’re exactly right…it’s been eating at me and I want to do something about it…this is how I’m going to get started…” She dug in and changed herself and her life quickly and permanently from there, losing 50+ pounds, growing her hair out and just looking great overall, getting together a strong resume and finding a job in a law firm, which then set her up to apply to graduate school and ultimately build a career as a trusts and estates attorney.

There are a few things I took away from our conversation last week, which got me thinking about several of these conversations I’ve had—both as the giver and receiver:

  1. The dynamic of opposites is interesting and powerful: Even though I was scared and felt bad about saying those things to her, she counts it as one of the kindest and important things anyone has ever done for her. Especially as women, we tend to rely on each other to tell us what we want to hear, make us feel good about our choices and our state of life, soften the facts and avoid reality, even if they might not be ideal for us or those around us. The interesting thing is that confronting her felt like I was hurting her or being mean to her, but instead it was the most magnanimous gesture I could have done for her at that point.

  2. Honesty is a privilege and a gift: If you’re in a position to help a friend, family member, or colleague with an honest point of view about their situation and what they can do to improve themselves and those who depend on them, you have an amazingly powerful and important opportunity. I’ve been on the other side of painfully honest advice and felt grateful as my sister did that the "coach” or advisor didn’t sugarcoat or "yes” me to death just to make me feel good in the moment, only to miss a chance to hit something head-on that needed to be addressed and improved. "Yes, your son needs help”…"Yes, you were too aggressive with your point and needed to let others weigh in during that meeting”…"Yes, you’re being unfair to your husband and you’re lucky to have him”…"Yes, you do have pit fat” ☺…"Yes, you’re too fire-ready-aim on projects”…"Yes, you’re starting to lose your ass and need to work harder to keep it”…I could go on.

All that said, doing this whole honest feedback thing right—both as the giver and receiver—isn’t a trivial exercise. If you’re on the giving end, it requires capitalizing on your emotional intelligence and best storytelling. It calls for compassion without caveats or too many fillers. It needs you to contribute specific suggestions and offer solutions and support.

One thing to consider if you’re giving the message is to think about how you’re going to achieve what a friend once called “the criticism sandwich” (cracked me up but it actually makes a ton of sense):

Start with,

"You do so many things well, such as…” or "I really admire how you do…”

before going into, 

"However, when you do this, things go wrong…” or "You would be happier/more effective if you…”

and then end with,

"Again, you’re such a strong person and I know you can overcome the challenge…I want to help you do it and this is how I think we can get started…”

Beyond the criticism sandwich, I wanted to pass along a few tips that I think are hugely important:

  • This is about them, not you:  Double check yourself to ensure that you’re NOT having this conversation for your benefit. This absolutely positively should not be about protecting or advancing yourself or making yourself feel better or more powerful. Instead, this conversation should be entirely altruistic and focused on helping the other person address a challenge that you believe is standing in their way of being happy/successful in life and you truly believe they have the ability to overcome.

  • Ensure your coaching is doable: Before providing guidance, make sure that the challenge is something the person can actually overcome. Help them focus on the good things that they can uncover, the things that they can control and that will make a meaningful difference in the way they feel about themselves, the way they interact with and experience the world around them.

If the tables are turned and you find yourself at the other end of one of these conversations, sit back, relax, and take them to heart. There’s no doubt that it’s human nature to be defensive (at least it is for me), to not want to believe what might be negative or not-so-great things about you, to maybe fight back in one way or another by gathering all the weaknesses the "coach” or advisor might have themselves, trying to find reasons why they’re not in a position to provide guidance to you. Or, you might immediately conjure up all of the examples demonstrating that what they’re saying isn’t true. And yet there’s a massive opportunity for improvement sitting right in front of you and a clear path to making yourself better while learning how to have a more positive impact on everyone and everything around you.

Where this has played out the most for me in terms of volume and frequency has been at work, particularly as I’ve become a manager of larger teams, but also as an executive working for other executives. I’ve been on the giving and receiving ends of some difficult conversations in my career and have realized that a hugely important success factor over the longer haul is the ability to give and receive tough love. Those who are able to achieve both effectively end up being able to manage up, down, and across masterfully. They can let team members know where they’re failing and how they can do better while maintaining a great relationship with them and even further the respect people have for them. They can become bigger and better leaders over time by really listening to critical, constructive feedback that’s given to them and adjusting what they do and how they do it while staying true to themselves and who they are.

Tough love…might seem like an oxymoron, but it’s a match made in heaven if done right. I still haven’t totally mastered it for sure, but knowing that it enabled me to help change someone’s life who I love and admire more than I can possibly convey feels like a million bucks. 

Thanks so much, Mo! I hope your recent gratitude for something that happened so long ago can help me support others in new, life-changing ways. 

xoxoxoxo, Weener ☺


About Christina


Christina Van Houten is the founder of Women at Work. Based in Boston with her husband and two teenage sons, she has spent the last 20 years of her career as a senior executive in the enterprise technology sector. Prior to evolving into tech, Christina founded a women's athletic apparel brand and served in several public interest roles focused on community and economic development. She started working at age thirteen and hasn't stopped since. She’s eager to help women find their way to the best possible life they can achieve.