Ryan Stephens Marketing

Ask the Tough Questions

14
July

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Guy Kawasaki had this to say about mavericks in big, traditional companies:

“They unleashed tough questions and critiques of their organization without losing their sense of loyalty to it. They asked the kind of questions every CEO should be asking. For example, Jane Harper asked of IBM, Why would great people want to work here?”

The thing is you don’t have to be working for Hewlett Packard or JC Penney to ask these kinds of questions.

I’ll be the first to tell you that something doesn’t have to be perfect before you run with it. Assuredly this blog post will be an example of that rationale. But you should poke holes and challenge assumptions before providing strategy for a client, or taking a product to market. Ask the tough questions. Ask the questions that most employees are scared to ask.

How many times have you forced a smile, nodded and told your boss something was a good idea when in reality, you thought it could use some tweaking, or worse yet, was absolutely ridiculous?

I don’t care what any CEO tells you. They want you to get wide-eyed, smile, and tell them their idea is brilliant. There are very few exceptions to this rule.

In most companies you have to pick your spots, but if you want to keep working for the same company your whole career putting out stuff you don’t believe in, you just keep nodding and smiling.

A few things:

Chances are your boss may be right. After all they’ve probably been at this longer than you, have more experience, more knowledge of the market, etc… I do hope this is true.

Even if this is the scenario and your boss is Brian Dunn, it still doesn’t hurt to push back when you get that uncomfortable feeling in the pit of your stomach. Your inquiries have the potential to bring up points of emphasis that may need to be fleshed out. More importantly, they provide you with the opportunity to show that you’ve genuinely thought in-depth about the project/deliverable, and also to learn from the responses of those above you (or fellow team members.)

Sometimes you’ll have the fortunate pleasure of providing enough logic and evidence to convince your superiors their idea is flawed. Chances are you’re closer to the project, to the client, and you handle more day to day interactions. Don’t be scared to speak up. Eventually your superiors will see the light. Some will offer a “good job,” and virtually all will claim the idea as their own when you’re not around.

Get used to it. Face reality. Employ the Canvas Strategy.

Maintain your loyalty, but ask the tough questions and critique your organization publicly. Do it so the company can grow, so that you can grow. Concede the little battles, but think of each instance as a strategic opportunity to learn more about yourself, about what you ultimately want to do in life. You’ll acquire the necessary knowledge and experiences to win the battle that counts: Your Destination.

Do you ask the tough questions? If so, have you had success with this approach? If not, why not? If you’re a CEO, do you welcome questions? Do you ask yourself these questions?

Photo Credit: Torley

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Posted on by Ryan Stephens

20 Comments

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  • http://anitalobo.posterous.com/ Anita Lobo

    Ryan,

    This post deeply resonates with me, as the person who usually asks the ‘why are we doing this question’

    Asking tough questions isn’t easy. It doesn’t make you popular. It doesn’t endear you to insecure bosses. It doesn’t make you the ‘friendliest’ person around.

    It does push you to find an answer [because no one wants to] and opportunities that may have been overlooked.

    In sum, asking tough questions gives you more ‘real learning’ in the school of life.

    Every great company and start-up teams that grow to be great businesses, have at least one person in the core team who asks the tough questions.

    Which also explains why so many companies have and continue to fail!!!

    So there!

    Thank you also for sharing the Canvas strategy!
    .-= Anita Lobo´s last blog ..[NEW] The simplicity factor =-.

    [Reply]

    admin Reply:
    July 15th, 2009 at 8:11 am

    @Anita – You’re obviously someone who has encountered this predicament because this comment is articulated so well. It’s so much easier to be indifferent, to want to play the “good guy/gal” role, but I think we have to keep the big picture in mind.

    Yes, you want the company to succeed, but chances are you won’t be there forever, and you have to learn and grow in the meantime so when you get to your next stopping point, you’ll be more prepared, more seasoned.

    [Reply]

  • http://thelostjacket.com Stuart Foster

    Loved the Canvas Strategy. Had never actually heard of it believe it or not. I tend to try and put my head down and run it through various surfaces/barriers. Sometimes I’m successful but most of the time I end up with a headache.

    Asking tough questions is extremely difficult for a lot of junior people for some reason. Stop being weaklings. Ask the damn question for the good of the company and yourself. Otherwise you will go crazy.
    .-= Stuart Foster´s last blog ..Why can’t we all just get along: Empowering influence on the Web =-.

    [Reply]

    admin Reply:
    July 15th, 2009 at 2:17 pm

    I’ve enjoyed watching you get progressively more brazen and outspoken as you’ve grown as a blogger. Always good to see passionate people exuding confidence.

    Surprised you hadn’t heard of the Canvas Strategy as much as you get around.

    [Reply]

  • http://www.jackieadkins.wordpress.com Jackie Adkins

    I think a lot of times people tend to internalize their disagreeance with people above them, which is probably unhealthy and isn’t doing anything to help improve the situation.

    I see two sides to this. One, the employee needs to approach asking the tough questions in a manner that is convincing and confident, but that is also respectful. If you’ve been internalizing this for a while, which probably has led to a little anger, you have to watch out for it coming off as challenging their authority.

    On the other side, although you don’t have control over this, the CEO, boss, whoever, needs to encourage employees to ask these tough questions and not come off as offended or mad that someone is questioning things. Sure, they’ll have to take an ego-check at the door for this to happen, but it will ultimately lead to more sound decision making.
    .-= Jackie Adkins´s last blog ..If you like an ad, does it matter? =-.

    [Reply]

    admin Reply:
    July 15th, 2009 at 2:43 pm

    Great contribution. I think these are good extensions to the conversation in that people should think about these issues prior to approaching a supervisor with a “tough” question.

    And you’re right. You can’t control their reaction either. This is something to be mindful of beforehand as well. I think that, like you said, we have to be respectful and in addition, leave our expectations at the door. You should ask tough questions for YOU and for THE COMPANY, but you can’t get bent out of shape if you don’t make progress the 1st time and/or everytime.

    [Reply]

  • http://www.scribnia.com David Spinks

    This is definitely an important issue for any company. I think that the reason so many don’t do it is because when they’ve tried to bring up hard, but important questions in the past, they’ve been shoved aside.

    Asking the question isn’t always the hard part…sometimes it’s having your question taken seriously that can be the real issue.

    @DavidSpinks
    .-= David Spinks´s last undefined ..(Enjoy 10 returned posts for 2 weeks) =-.

    [Reply]

    admin Reply:
    July 15th, 2009 at 2:53 pm

    Like I mentioned in response to Jackie, I think you just have to be mindful of the things you can control. You can’t control your supervisors reaction, but I think unless you’re dealing with a real stubborn egomaniac or you’re in a big company with too much red tape it’s all how you frame it.

    If you tell a compelling story that sheds light in a way that forces them to understand your vantage point you may gain enough momentum to break it wide open.

    Do you have any additional insights into how ‘green’ employees or people that have been shoved aside in the past could approach this scenario?

    [Reply]

  • http://www.smallhandsbigideas.com Grace Boyle

    We are taught to respect authority and elders. Those are rules of thumb, but of course, differ depending on the person. I think respecting authority (and also fearing them) needs to find a balance.

    When my CEO or boss brings an idea to the table that I somehow disagree with, I appreciate that an honest opinion is welcomed. I do agree that without a doubt, my CEO knows more than me. However, I think there are pieces of the company or new fresh ideas that I might be able to offer so if I strongly disagree with something, I speak up. I do it with tact and offer an alternative idea instead of just saying, “No, I don’t like it.” Standing up for yourself within reason is why some of the greats got to where they were. Nodding and smiling is bullshit, to me at least…

    It’s almost like, there are no stupid questions. I think there are no stupid ideas. Unless you speak up with your idea or thought, you will never know what might have happened or someone else might already think of it.
    .-= Grace Boyle´s last blog ..I Want to Hug Alice.com =-.

    [Reply]

    admin Reply:
    July 15th, 2009 at 2:58 pm

    @Grace – Excellent point re: not just saying you don’t like an idea, but offering an alternative. It’s easy to discredit someone else’s ideas, but what’s the point if you don’t have any insight that can take it in another direction, improve it, etc.

    Some of the things we’re all circling around is that your approach is important if you’re going to ask the tough questions. Tact is important.

    [Reply]

  • http://www.opheliaswebb.com Elisa

    I’ve got to say I’m amazed with how many managers/owners/CEO’s suffer from Rose Colored Life. I don’t know if it’s that they’ve had to work so hard to get where they are, but a bunch that I’ve run into in the past few months just don’t WANT to hear about the things that need to change. They want everyone to be happy with their job, they want the clients to break down the doors (in a good way,)they don’t want life to be challenging.

    That being said even they know deep inside that isn’t the way life is. A rose colored view generally means you have cataracts or something, and that’s not good. I would, however, offer this piece of observation on asking the “tough questions.” Ask tough questions with short, open ended questions that will help your higher up realize on their own the viewpoint you are presenting. It will be a much better “sell” than telling them why you think so. Additionally, the BEST open ended questions start with how and what NOT the word why. Why is reserved for 5 year olds wanting a cookie before dinner. How and what help to build the vision and discover the strengths/weaknesses “How will that look…what is the final outcome we hope to see here”

    [Reply]

    admin Reply:
    July 16th, 2009 at 11:31 am

    Definitely some solid, practical advice there Elisa. (I’m going to have to start editing the posts and adding some of these awesome comments you all keep delivering into the actual posts.)

    I’ve always really enjoyed the teachers, mentors, etc. that make us learn so much more by challenging us with questions instead of giving us answers. I think this is a skill you have to acquire, but using the same approach to superior definitely seems like a viable tactic worth exploring.

    [Reply]

  • http://www.lifewithoutpants.com Matt Cheuvront

    There are VERY few CEO’s who welcome in new ideas and welcome innovation and new approaches from their staff. Clearly I don’t have the tenure to back up the above statement, but from what I have gone through and seen others go through, when you’re at the bottom of the totem pole, you’re really at the bottom, and you’re treated as such. But, while CEO’s may have a right to be ‘right’ – it’s the ones who are at least willing to entertain new ideas from their crew that truly succeed. You hire (hopefully good) people for a reason – you do it because you believe they will bring value to your team, that they offer something unique and special. My memo to the CEO’s – Expect your employees to do what they were hired to do, but let them exceed expectations, promote a creative environment, and encourage innovation.
    .-= Matt Cheuvront´s last blog ..The Treacherous First Step =-.

    [Reply]

    admin Reply:
    July 16th, 2009 at 11:37 am

    I feel some animosity towards an old boss coming out there Matt. A bit off topic from the ‘asking questions’ topic, but per usual you’ve provided solid insight we can all learn from. Besides that’s what the comments are for, extending the conversation.

    I think if you look at a lot of companies, particularly smaller ones the CEO who hires the right employees and then listens to their ideas, their push back, etc. (i.e. learning from employees) are the ones who invariably “make it big.”

    Even to the point of productivity. Some employees constantly ask themselves what’s in it for them. Sure they’re getting paid, but that’s not enough anymore. If there’s not an incentive to go above and beyond, if you don’t believe in the company or share their values most people will do their job, but NEVER once think about going above and beyond.

    [Reply]

  • http://www.owlsparks.com/ Carlos Miceli

    I remember a blog post from Ben Casnocha, talking about a book that he read, that said that questions are the important part of education.
    We are constantly learning how to answer, instead of how to ask. And this is a crucial mistake, because progress lies in a question, in someone showing us a new door.
    Education, work, personal philosophy, it’s all the same. questions rule.
    .-= Carlos Miceli´s last blog ..You Can’t Handle The Truth =-.

    [Reply]

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  • http://dannybrown.me Danny Brown

    If you don’t ask the questions, how will a company ever make their business the place people want to work? Where they know their ideas/concerns will be listened to? Always ask the tough questions – otherwise you may as well just go and work at News International… ;-)
    .-= Danny Brown´s last blog ..The Ego Has Landed (Or Has It?) =-.

    [Reply]

  • http://www.managingactions.com Erich Stauffer

    Knowing what questions to ask is sometimes the hardest, but most critical part, of any organization. If you start with the question most asked of yourself, “What do you want or desire in life? What is your purpose?” That answer may take years or a lifetime to answer, but those who find it and answer it early will be the most successful.

    In the same way, when leader or maverick within an organization asks questions that will lead to success, they will inevitably be hard to answer, but the rewards will be success for that organization. You might say that questions and answers are the ying and yang of success.
    .-= Erich Stauffer´s last blog ..The Gristmill at Spring Mill State Park: Mirror Matter Moon =-.

    [Reply]

  • http://anitalobo.posterous.com/ Anita Lobo

    Had to get back here to share this:

    @paulocoelho An interesting life is full of questions.
    A boring life is full of answers.
    .-= Anita Lobo´s last blog ..My new post on India PR Blog =-.

    [Reply]