on being assertive: tips + advice from two top agency executives

Working Desk

For most of my career my mentors and sponsors have been men. In 1997, I entered the workplace in an age where women were just starting to experience the taste of leadership, when they were told by various books and handsomely-paid speakers that they could “have it all” if they were ambitious enough. We had finally recovered from the cruel sartorial joke that were shoulder pads, yet most women still wore tights and sneakers on the subway. Having studied business with both men and women, have interned at some of the most prestigious investment banks alongside men, I didn’t yet understand that there was an invisible line between men and women. In the age of Bill Clinton and this burgeoning phenomenon called the Internet (we had one Internet terminal at Chase when I started and nearly all of us used Lotus Notes for email), I walked into the workplace blind. It was only when I noticed that I was one of few women in banking, it was only when I noticed the ascension of men to higher ranks with ease while women had to constantly prove their worth did I recognize that the divide, although in start contrast to years past, still existed.

It existed when I was #3 in an agency and I noticed that my aggressive, ambitious behavior was admonished while the same behavior from my male counterparts was praised and fostered. I felt that it was not only important that I be admired, but as a woman I must be liked; I must play nice. I must be the caretaker and nurturer while my male counterparts weren’t expected to assume the role of mother in the workplace. I must be assertive, but not too assertive, and after a while I started to get really frustrated.

Really frustrated.

That’s when I encountered my first extraordinary mentor, Anne Bologna. Anne is a bucket of awesome. She’s smart, passionate, assertive–all the things I want to be as a leader, but she doesn’t compromise. She refuses to play into a gendered role, and has given me confidence in my voice, my role, and more importantly, how to speak up for what I want and deserve. She was responsible for getting me involved with StraightUp, an informal organization that focuses on fostering women execs in the agency world. While I’m no longer interested in being part of the agency structure, the network and the advice are invaluable.

I’m really thrilled to share some tips and advice from a recent StraightUp discussion with Sarah Thompson (Global CEO of Droga5) + Emma Cookson (until recently Chairman of BBH New York). I was unable to make the event because I was stuck in a Miami airport, cursing out American Airlines (never again, people. NEVER AGAIN WITH THIS AIRLINE), but they were kind enough to share the notes from the meeting and they gave me permission to reprint them for you guys. Enjoy!

1. Being Assertive One-on-One (e.g. Negotiating a Raise/Promotion)

  • THINK OUTCOMES. Always decide beforehand what you want the outcome(s) to be. You’ll seem less in control if you go into a negotiation without that clarity, or if you go in thinking “I’ll see what (s)he suggests/offers after we’ve discussed everything”
  • SPELL IT OUT. Don’t assume they remember your track record or your merits. No one has time to care as much about you as you do. Remind them. Doing so is just confident and efficient. And it doesn’t have to come across as arrogant (make sure it doesn’t–you don’t need to be a d*!k) e.g. “When I look back over the last 6 months, what I feel most proud of is X, Y, Z”. “When we last talked you encouraged me to do X, Y, Z – which was really useful perspective and helped me achieve X, Y, Z”
  • GET THEM TO TALK FIRST. Typically, by asking questions upfront–even if just something like, “Before we start, can I be clear about what would you like to get out of this meeting?”/”How do you prefer to handle this sort of meeting”? etc. It is much easier to navigate a negotiation if you know the other person’s ingoing views and assumptions, and the tone they are going to adopt. So try to resist responding to questions that ask you to commit to your views before hearing a bit from the person you’re negotiating with PREP SOUNDBITES BUT NOT A SCRIPT. Have the (few – 5 or 6 ish) key points you want to make planned out in advance. In soundbites–so they are memorable and super-clear. Ready to use. It helps you feel relaxed and ready, and prevents you forgetting to cover a key point. But *don’t* plan a ‘speech’: if what you say is scripted, it will sound scripted–and sounding scripted sounds vulnerable.
  • PLANT SEEDS. Talk way ahead (months, years!) about your future ambitions–“one day I want to be head of dept”–so a path is carved out. A request is much easier to say yes to if it doesn’t come out of the blue. And a promotion/raise is much easier to give if you’ve known for months and years that the person seeking it is clearly ambitious.
  • 2. Being Assertive In Meetings

  • START SENTENCES RIGHT. Don’t start sentences with “I think”, just make the point. Same thing with ‘Do you think that….?”. And definitely avoid, “This might be stupid but…”: we all do it, but it means you’re immediately selling short what you’re about to say and making people question your self-confidence and competence. Really: it feels comfortable but it isn’t effective.
  • SPEAK EARLY. Try to find something to say early in a meeting–even if casual/trivial. Just hearing your voice aloud will make you feel more comfortable and will transmit that you are at ease/assured. And the longer you wait to say something, the more pressure that’s put on what you actually say eventually to feel impressive. REMEMBER YOUR CONTRIBUTION DOESN’T ACTUALLY HAVE TO BE BRILLIANT OR NEW IN ORDER TO IMPRESS. You can also confirm and/or question. e.g. Say out loud that you think what X just said was exactly right, for X reason. Or ask for something to be clarified. (Come to the meeting with questions prepared.)
  • PREPARE TO BE DIRECT IF OTHERS ARE AGGRESSIVE/DOMINEERING. Prepare specific phrases to deal with times when others are talking over you or taking over. And practise saying them out loud in advance so you know they’ll feel comfortable coming out of your mouth, e.g. “I don’t think this is a productive conversation.” Or “I haven’t finished ….”. Or, “Yes, I already said that.” IF NECESSARY, LET IT GO TO SHIT. If a meeting (or indeed a bigger situation) is just totally messy, rambling and/or out of control, don’t automatically jump in to try to help. Sometimes it’s better to let it go to shit. Don’t get involved if doing so risks you getting positioned as part of the mess/confusion. Stay quiet and aloof. Then intervene right at the end–or afterwards–with a concise observation and clear proposal to get to the right outcome. IF YOU ARE PRESENTING, TRY HAVING YOUR FIRST 2-3 SENTENCES MEMORIZED VERBATIM. That way, even if you are so nervous you lose all confidence and clarity when it gets to your section, you will still start off ok. And as soon as you hear yourself sounding OK–even just for a sentence or two–it will calm you and help you get into your stride
  • 3. Being Assertive Generally, Day-to-day:

  • BE YOURSELF. Although easy to say, hard to do–this one is vital. Don’t try to be someone you’re not. It just doesn’t work: you can always tell if someone is ‘adopting’ a style consciously–‘trying to be assertive’–and it just comes across as uncomfortable and unconfident, so it undermines your credibility. You can assert yourself in so many different successful ways, find your own: feisty and pushy? cool and unrufflable (often done successfully via strategic use of staying silent)? nonchalant and genial? You have to find your own personal style for being assertive/assured and it may not be at all aggressive.
  • DON’T CRY WOLF. In general, try to stay on even keel in your daily work so that when you really need to make a point/make something to happen, you can get loud and/or stroppy and it will be meaningful.
  • PRAISE YOUR TEAM. Publicly celebrating your team’s achievements (e.g. via an email to senior management) reflects well on you as well as them. It demonstrates personal confidence/leadership. And it is just the right thing to do….(In similar vein, a great way to be assertive in a meeting is to spot some other person who’s clearly trying to make a point but not getting heard – and make space for them: “I think Karen has something she’s been trying to say – Karen, what was it you wanted to add?”)
  • BE DISARMINGLY HONEST. This doesn’t work for everyone, but sometimes if you’re nervous or stressed it can help to just own it and be honest. There is a confidence in being able to admit your vulnerabilities without fear, no-one’s perfect, e.g. “I must admit I’ve been very apprehensive about this meeting…”, “As you can probably tell, I’m finding this situation very stressful…”
  • Photo Credits: First image via; Second image: Death to the Stock Photo.


    7 thoughts on “on being assertive: tips + advice from two top agency executives

    1. Thank you for the excellent advice! I especially like the “think outcomes” point.
      Are there any blogs and online resources that you go to for career related inspiration that you would also recommend?


      1. You’re welcome! Let me put some thought into this. At this stage in my career I tend to read articles in journals rather than go to websites. I normally peruse HBR (they have the best management and leaderships articles on and off, IMO). I also really like Fast Company, Inc., Entrepreneur, Business Week, etc. I personally tend not to go to blogs for career advice, but I know a lot of women quite like Levo League. Sorry! I wish I could be more helpful. If anything comes to mind this week, I’ll update the post to include it.

        On Mon, Mar 16, 2015 at 12:08 PM, love.life.eat wrote:


        Liked by 1 person

    2. Mhm, will have to see if I hit any of those points or not and what i can improve (there’s always room, right? :)) ). Thanks for the great article, hope to see even more great advice from you in the future. 🙂


    3. Hi Felicia! I saw your tweet for feedback on the usefulness of these posts, can I just give a resounding yes and ask that you please keep them coming? And thank you so much for sharing, it’s very generous of you.


    4. Great tips. I’m going to share them with my daughter even though I have a feeling she may not need them. She’s an accountant and chief comptroller at a Colorado energy company and she’s been fortunate enough to have worked with and for powerful women in almost all of the jobs she’s had.


    5. Pingback: Weekend Reading.

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