The super secret key to success: Ask!

Published February 22, 2017   Posted in How to Think

Hard work. It’s great in theory, but the years I spent meandering my way through corporate America taught me that success very rarely resembles the fluffy fairy-tale idea that success comes to those who “work hard”. Or even “smart“.

More times than not, success comes to those who ask for it.

If you think that you are ready for a promotion, ask for it. “But it’s outside of our promotion cycle,” you may retort. Who cares. Ask for it anyway. Your employer recognizes those who are proactive. Even if you don’t get a promotion immediately, the seed has already been planted. You’re setting the course.

Hard work is bullshit.

Okay, not entirely bullshit: If you come into work an hour late and twiddle your thumbs all day, you probably aren’t going to get a promotion. In fact, you should feel damn lucky that you even have a job. You do need to be at least somewhat productive. A positive contributor. A reason to collect a paycheck. As I wrote about before, it doesn’t take all that much to look good at work these days.

The idea that if you work hard, “success will come to you” is devastatingly attractive, but does not represent how businesses promote their staff. I used to be in the position to promote until I demoted myself. I’ve seen this work first hand – from both sides.

Success does not become you

Waiting for success to happen is a game that we will lose almost every time. Don’t wait for things to happen TO YOU. Instead, go after what you want. Be proactive and be sure that your employer knows your professional goals. Give them a reason to promote you. Quit waiting for good things to happen.

The longer you wait, the steeper your climb to the top.

Here, let’s get more specific.

Want success? Ask for success!

Good things come to those who ask for them. It’s remarkable. In fact, about half of my promotions and raises throughout my working career in corporate America have come as a result of me asking. Asking means you’re serious. It shows your organization that you are a productive team player who wants to contribute more (or feels undervalued). Either case can be incredibly persuasive.

Before you ask, be sure to understand the following tips.

Know what you want

Before asking for success, know what success means to you. For example, do you really want a management position? If so, know what you’re getting yourself into – at least to the best of your ability. Picture yourself doing the job, not just enjoying the title. I fell into this trap, and trust me, it was a painful lesson! More on this tip below.

Be confident

Believe you’re the best motherf-er in the room. Seriously, believe it. Those who exude confidence are natural leaders. It shows. Even if you’re wrong, the confidence to make a decision and pursue it full force is what separates followers from leaders. Remember: I’m talking about confidence, not arrogance. Don’t be a prick. This isn’t about talking over people or shutting down conversation or debate. In fact, it’s the opposite. Start the conversation and lead the debate with respect and honesty. Engage those around you and get them involved.

Basically, do what leaders [should] do, even if your official title doesn’t include “manager” or “director”…yet.

Act like the person you want to be

If you want to be the leader, act like the leader. Don’t ask for a promotion into management and then continue doing what you’ve always done. Take the initiative. Volunteer to help your coworkers. Brainstorm ideas. Offer your suggestions. Be up front about your willingness and ability to lead. Help your manager in any way that you can. Most people are all talk and very little action. Make it obvious you’re about action by separating yourself from the pack.

One of the best pieces of advice I’ve ever received came at one of my former jobs. I asked for a promotion into a position that sat vacant, but the organization was not ready to make a change – yet. I asked what I can do NOW to better equip me for the promotion later. The answer I got was simple and direct: “Pretend you have the job“. I stepped up and accepted the responsibility of that position before I even had it. Within a couple of months, the position was mine. True story.

Do not fear failure

Those who are afraid of failing rarely get to where they want to be. The reason is simple: When people fear failure, they resist taking risks. They refuse to put themselves out there. They remain huddled in their comfort zone waiting for something to happen to them.

This natural but devastating habit keeps us from taking risks and going after what we want out of fear that things might not work out perfectly. I have a secret to tell you: Perfection is unattainable, so stop trying to get there. You WILL fail. It is a natural part of life. I’ve failed. My neighbor has failed. We ALL have failed. It happens. Get over that fear – fast.

If you want something bad enough, go-the-fuck-after-it. Make it happen. If you fail, you fail. Big deal. Try again next time.

Be prepared to back it up!

If you stroll into your manager’s office to ask for a raise, be ready to back up your argument with facts. Pick out the times where you went the extra mile to help on a project. Those 60-hour weeks should count for something. That uncompromising deadline that you met? The report you pulled out of your ass but knocked the socks off of that client? The new business you brought in? Yeah, this stuff.

Before meeting with your manager, know your facts. Rehearse. Play devil’s advocate and practice your answers to likely questions or concerns from your manager. Also, decide what you’re willing to compromise on. If you ask for a $10,000 raise but only get $5,000, is that good enough? Be direct, firm and confident.

Don’t look stumped.

Remember: Even if you don’t get what you want immediately, the seed has already been planted. Your manager knows what you want, and organizations tend to have more flexibility in how they promote than they care to admit. If your manager is afraid to lose you, he or she may go to bat for you to make sure you get what you want during the next raise cycle.

If a promotion comes down to a choice between two equal people, the person who asked for it will nearly always get it. Guaranteed.

Be careful what you ask for because you just might get it

I wrote about my high-level IT directorship position before, but it is appropriate to rehash here. At the time, I spent the last eight years of my working career as a follower. I was ready for additional responsibility, and there was a sea change in the organization. The position was mine because I asked for it.

Unfortunately, I soon discovered that high-level management isn’t for me. I hated answering questions to unknown problems. The organization wanted commitments to unreasonable projects and demanded acceptance to policies and procedures built by those without a shred of information technology experience. Some days, it was grueling. And, my staff had no idea.

The performance reviews were mind-numbing. My staff didn’t care because it was a check in the box. I didn’t care because it was a check in the box. Human Resources didn’t care because it was a check in the box. Management nonsense, day after day. Paperwork. Problems. Meetings. Coercion.

I was blinded by the title. I wanted to try my hand at being “the guy”. To call the shots. To make the decisions. Finally, to be the guy that everyone else smiled around.

Management isn’t for me. I tried it. I could not get on-board with doing that job for the rest of my life. I left my position and pursued a work-from-home job that paid better and lead me straight into retirement. I decided what I wanted and I went after it.

Moral of the story? Be careful what you ask for. Whether it’s more money, a promotion or anything else, be prepared to do the job. To put up or shut up. You may have a whole new set of problems to content with. More responsibilities. Later nights. Longer weeks. More travel.

You get the idea. Be prepared.

Edit: Based on a comment from Mr. Tako Escapes, I feel compelled to mention that some organizations may retaliate against your request for more money. While in my personal experience this has been the exception rather than the rule, it can happen. Know your organization well. I might argue that if your organization would retaliate against your request, it may not be the right place for you anyway.

Have you ever asked for a raise or a promotion? If so, how did it go?

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38 responses to “The super secret key to success: Ask!”

  1. Very good summary, starting with the very good point that the squeaky wheel gets the grease, or the job as the case may be. I might add one thing to it. If you really want to move high, go wide not deep. That levels not for everyone, but if that is the goal most upper level management folks are looking for a breadth of experience over experts in a specific widget.

    • Steve says:

      That’s very true, FTF. Very specific knowledge is good for very specific kinds of jobs. Management, very often, needs folks who are widely experienced in most areas of business. 🙂

  2. Go Finance Yourself says:

    Great advice, Steve. What I struggle with the most is trying to make everything perfect, which leads to a fear of failure. Sometimes I have to kick my subconscious in the ass and just dive right in so I’m not paralyzed when a situation isn’t perfect. Showing what you bring to the table and asking what you want is key in any walk of life. If you’re a great guy but are too afraid to ask a girl out, then she’s not just going to magically come to you.

  3. Jim Wang says:

    Hard work is easy advice to give, that’s why everyone says it! 🙂

    The reality is that you need to make your own way. Every construct that exists was made by people and can be broken by people just as easily. If you were going to be poached by another company, would your boss say “sorry, we can’t do anything to try to keep you, this is outside our ‘poaching from another company schedule’? so bye” — no.

    Of course not.

    • Steve says:

      Ha! Good point, Jim. The fact is people, just like most organizations, can do whatever the hell they want to do. Policies be damned. If something is valuable enough, they will find a way to make it happen. 🙂

  4. I’ve always been intrigued by how many people claim to WANT success and how few people ACT on that desire. Success is elusive enough, at times, even if you’re busting your butt and making it known to everyone who matters that you want that raise, promotion, etc. Waiting around for good things to happen doesn’t work, but that’s what many people do.

    I have to agree with you about the managerial life, Steve. Much like you what you described, I moved into a similar position but didn’t really have the opportunity to do much leading. I was constantly told to take initiative, yet my supervisor complained that I was overstepping when I did so. Pushing paper was by far the worst aspect of that job. But I’m glad I had the experience because it helped me redefine the paradigm of success I had shaped for myself.

    • I agree with Superero here about pushing paper in the job he was in (and I am currently in). Moving into administration was one of the best and worst things I could have done. I was “tapped” to be put into an administrative coursework program and gladly took it and ran with it. I am a strong leader in some ways – but not in others. But I never would have known it if I just kept teaching for 32 years. I also doubt I ever would have considered retiring early without the move into administration, so there’s definitely an upside to that decision too!

      • Steve says:

        Amen to that, Vicki. I think my move helped push me towards early retirement as well. And I think that’s one of the morals of the story about corporate America – the more you move around and try new things, the more experienced you get and understand what is truly important to you.

    • Steve says:

      “But I’m glad I had the experience because it helped me redefine the paradigm of success I had shaped for myself.” – Absolutely spot on. It did much the same for me as well. I didn’t like the job, but it definitely taught me a great deal about working in corporate America from the other side.

      Sometimes, it’s better to DO the work than to MANAGE it.

  5. Great post! I agree, I’ve always found it best to be transparent about what I want and why I deserve it, especially with a boss whose trust I’ve earned. However, I do have a caveat. In some organizations, there is a distinct culture that must be understood and managed to a certain degree. I’m in a large organization with a distinct culture, and there are cultural realities to deal with at every level, from leadership on down. There can be a competition for personnel and resources that you’re not even aware of until much later on in the game (and you might be a pawn in that game). It’s not always cutthroat, it’s just the way it is. What I’ve learned is that when my boss is behind me and the winds are favorable, I push hard. When my boss is lukewarm and the winds are not favorable, I bide my time. Good topic to think about .. –R

    • Steve says:

      That’s smart, Rich. There are definitely wrong ways to go about this, and understanding your organization and how it operates is the key to getting what you want. It is amazing how much goes on above your level…things you have no idea are happening until you’re there. I found that out, too, when I served as the Director. It’s definitely something that I never want to experience again!

  6. I’ve asked and I haven’t received, though there is one in the makings for me in April. We will see how it goes. With more money, comes more responsibility. At this point, I want to explore opportunities outside of the work place – leveraging my paycheck and time to build platforms and passive income on the side! Exciting times we live in… W2’s aren’t for everyone!

    • Steve says:

      Ah – “Ws aren’t for everyone” – love it! And I agree, they aren’t. I think you hit the nail on the head about knowing what you want. More money often does come with more responsibility. But, when people focus solely on the money, bad things happen…and quickly.

  7. thefiteacher says:

    What about working for school districts? That’s where I’m at. I find your philosophy still sort of applies. If not exactly “asking” for your promotions, then seeking out ways to get those promotions WITHOUT asking. For example, there are all sorts of hidden programs that will pay you for getting your masters, running some races during the year, coaching, etc. And no one can say no to these “requests” for raises! Booyah!

    • Steve says:

      I certainly can’t speak for *every* industry. Ultimately, understanding your organization/industry will be your best tool to getting where you want to go. I can definitely see how those kinds of school opportunities can lead to bigger and better things. 🙂

  8. ianbond2017 says:

    I was a great producer who was asked to join management. A mentor told me, “Never give up your book.” To this day I enjoy client work more than the endless meetings, performance reviews, and political crap involved in senior management. Mind numbing is being kind.

    I would only add, also be very careful when you’re asked too!

    Great stuff.

    • Steve says:

      Thanks Ian – you’re right, timing can be everything. Ask at the right time and you improve your chances of getting what you want. No doubt about it!

  9. Mrs. BITA says:

    This is an area I struggle with. I feel weird and awkward when I think about asking for a raise or a promotion. I’m pretty sure that this has cost me over the years. I need to get over myself and play the game the way it is meant to be played.

    • Steve says:

      A LOT of people have that same apprehension, Mrs. BITA. People undersell and undervalue themselves all the time. It definitely takes some time (and practice) to master, but once you do, it immediately gets easier.

  10. Really good advice. One of the common traits I’ve seen among “successful” people (as measured by traditional career track-type measures, which aren’t quite what I would call “success” but are helpful for accelerating the path to FIRE) is self-advocacy. I asked for a raise once, and I went big — practically asking for my salary to be doubled. It wasn’t particularly well timed, it took months of negotiating and building my case, and I didn’t end up getting nearly what I asked for, but it did get me a raise and more recognition for my contributions. Well worth the effort. You’re right that you might not always like the end state, but then you can always make another change.

    • Steve says:

      Nice, Matt! Go big or go home, I guess. You chose to go big. And like you said, getting *something*, even if it wasn’t exactly what you asked for, is definitely better than nothing. 🙂

  11. I’ve never asked for a raise while at a job (not a long enough history), but I’ve done tough negotiations while accepting positions. I’m a woman, so I’m hyper-sensitive to the pay gap issue, so I fight for my pay.
    I’ve been undercut twice and completely walked away from the deal. The companies came back with higher offers each time. Sometimes you have to play hard ball and follow through with consequences if you can’t get what you want.

    • Steve says:

      That’s perfect, Mrs. Picky Pincher. Be prepared to walk away. And like you’ve noticed, negotiating a bigger salary going in is your very best tool to making a ton of money. Counting on raises doesn’t work quite as well as going in with a bigger salary. Get it from the beginning! 🙂

  12. Great in theory Steve – hard to implement in real life. At some jobs, I’ve asked for both promotions AND raises and never received any, despite asking. It’s not like I was a slacker either. It just depends upon your manager, and the environment your business operates in. Sometimes businesses literally don’t have extra money for raises and promotions.

    It’s also worth mentioning potential negative repercussions for asking for raises. I was literally fired once for asking for a raise. This was after getting promoted two years in a row. Ask for a raise, and then boom… fired a week later for no discernable reason.

    It does happen.

  13. GrievingDads says:

    Great article and one I certainly relate with. The old me constantly wanted to be given the slap on the back as the guy that gets it done. I use to feed off of that type of recognition (along with the increase in pay). However, that all changed for me after I lost 2 children over an 18 month time frame. That was in 2004 and 2006 and over the last 10 years I’ve hit rock bottom and have bounced back with a new outlook. Corporate BS is just that, BS.

    I am currently in a corporate job and have turned down many opportunities to “move up the ladder” or on to other organizations for larger roles. I have a completely different perspective on what is important in life now. I do my job, but I don’t kill myself and I don’t take it home with me. But I do just enough to still be an important player in the organization. I have since written a book for grieving dads (Grieving Dads: To the Brink and Back) that has made its way into the hands of the men who need it around the world. I hear from men everyday trying to survive the aftermath of losing child and I received a sense of purpose through my work with grieving dads.

    There was a time I wasn’t sure if I was going to survive the losses. It brought me to my knees for several years. I made a commitment at that time that if I survived it, I was going to work towards living a life compassion and being free and clear. I never want to feel owned or in a position that I can’t take time to weather a shit storm when they hit, believe me, they will. I am proud to say, I will be free and clear at the end of this year. I will be able to walk away from the corporate paper pushing job and pursue something much more rewarding that allows for freedom.

    Thanks for the article.

    • Steve says:

      It’s funny how our perspectives change, isn’t it? And I’m totally with you in regards to moving up the ladder. Been there, done that. It ain’t as fun as it sounds. It does depend on the organization that you’re at, but “at the end of the day”, management is management. You gotta be cut out for that stuff. I’m definitely not.

      “I never want to feel owned or in a position that I can’t take time to weather a shit storm when they hit…”

      Well said, my friend. Well said.

  14. TheRetirementManifesto says:

    Great post, Steve. I once approached the President of our North American business and asked to be consider for a Plant Manager role which had opened up. I was in Sales at the time (NOT the normal place they’d pull somebody from to run a plant!).

    I got the job.

    My career took off.

    The rest is history.


    • Steve says:

      Thanks Fritz! It’s funny how powerful just asking for something can be. If you express interest in something bigger and better, MOST people respect that sort of thing. 🙂

  15. Raises, I haven’t succesfully negotiated. But I’ve generally done alright at positioning myself for promotions. Success requires both hard work and good fortune. I have experienced both fortunately, but could as easily have worked as hard and not gotten the same lucky breaks. Working for good leaders makes a difference!

    • Steve says:

      Hi Sarah – I definitely agree that working for good leaders makes a huge difference. Fortunately, I’ve worked for more good leaders throughout my career than I have bad. 🙂

  16. Miss Mazuma says:

    Gotta love corporate America! I truly believe that there is a way around most things. I have heard so many stories about people interviewing for jobs they weren’t qualified for but getting them based on personality, raw talent, or persistence. It truly does pay!! Hmmm….which now that I think of it, perhaps it will come in handy to just ask about a little idea I have. Lately I have been talking to a lot fo new hires about money – they are absolutely clueless about our 401k options, ESPP, and other retirement benefits. I have an idea to come up with a class for new hires to attend as they go through training. Maybe a one or two hour more in depth overview. I have been talking myself out of it because I don’t have a background in finance, or any education really, but perhaps I should just put it out there and see what happens? What’s the worst they can say?

    • Steve says:

      Good on you, Miss Mazuma! I think that’s definitely a worthy proposition. You’re right, most people don’t really understand that stuff beyond simple “retirement savings”. I’d say explore your idea and flush it out (if you haven’t already) and see where you might be able to provide that value. You just never know!

  17. We can definitely relate to the “be careful what you wish for” statement. A few years ago my wife advanced in her job to become a supervisor. She loved the work but soon became fed up with dealing with the daily drama of her employees. It really started to consume her to the point of switching jobs to get out of the supervision role. I hate to say never but I am confident to say she will never do that again. Great post.

    • Steve says:

      Thanks Defined Sight. Your wife experienced what I experienced. It was fun at the beginning because it was new and exciting, but once the routine set in, so did the monotony. Management definitely isn’t for me.

  18. ajfichter says:

    Performance reviews are simply checking a box for all parties involved. So true…so true. My organization takes it a step further and has HR conduct discussions with all teams (management is not present for these discussions), to obtain feedback on what management can do better. I try to be optimistic that positive change will come about, and I give my honest feedback, but it really is just lip-service. I’ve been through enough of these cycles to know that nothing really changes, and unfortunately, there’s a better chance that what you say will be used against you than it will be used to make things better.

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