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Cigars, Whiskey and Winning: Leadership Lessons from General Ulysses S. Grant

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Long before leadership became identified as the catalyst for corporate success, the Civil War's winning general was showing the world how dynamic leadership is the crucial determinant of victory or defeat.Ulysses S. Grant never sought fame of glory, nor did he try to tie his performance to personal reward. Instead, he concentrated on contribution and service. He looked upon being given increased responsibility not as increasing his power, but as increasing his ability to get the job done. "The great thing about Grant...is his perfect correctness and persistency of purpose." (Abraham Lincoln)

In this masterful retelling of Grant's story, Al Kaltman draws on Grant's writings and life experiences to present a series of practical lessons on how to get superior performance from the troops.

Going beyond mere "how-to's", Cigars, Whiskey & Winning deals with character traits, core beliefs, and fundamental values to reveal the secrets to becoming a winning leader that are as much about "who to be" as "what to do". And there isn't a chart, table, or checklist in sight-just a handy index of lessons for ready inspiration on demand.

322 pages, Paperback

First published January 1, 1998

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Al Kaltman

6 books

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5 stars
96 (36%)
4 stars
105 (39%)
3 stars
54 (20%)
2 stars
9 (3%)
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Displaying 1 - 27 of 27 reviews
84 reviews9 followers
October 4, 2021
Unique history/managerial leadership book. Easy read and quite interesting. This would be a good “one lesson a day” read before work. Much respect for Grant.
Profile Image for Scott.
1 review2 followers
June 17, 2019
I learned so many lessons about leadership, communication, organization, and character from this book. I always thought of Grant as a heavy drinker who led by being "one of the boys". He was so much more than that.
Profile Image for Michael Brady.
253 reviews37 followers
April 1, 2012
This analysis of the life, career, and leadership style of one of the United States’ most successful generals (and least successful presidents) is a quick, informative, and thought provoking read.

Using the military career of Hiram Ulysses Grant as a framework author Al Kaltman has created a quick reading combination of biography, historical analysis, and a guide for leaders. By using the life of one of the Civil War’s key figures as a backdrop Kaltman engages the reader by showing that a leader’s effectiveness can be a life and death matter. In doing so the author dodges a common fault of many management and leadership books and creates a connection between common sense practices with real world results.

Such a bracing read may be a little too much for sensitive folks who do not believe managers in their corporation deal with conflict and risk on a daily basis. Those of us in the security trade however not only believe it; we thrive on the fact of it.

Across 11 chapters Kaltman moves chronologically through Grant’s early military career, his failures, his return to the Union Army in 1861, his successful prosecution of the nation’s most disastrous war, and its aftermath. The author breaks the chapters into different lessons:

Seize Opportunities
Failure
Turn Mistakes into Training Opportunities
Know Your Competition
See the Total Picture
Don’t Scatter Your Resources
Shatter Paradigms
Pounce on Your Competition’s Blunders
Focus On What You Could Be Doing
Develop an Alternate Plan
Always do what’s Right

All lessons are as applicable today, especially in the guarding industry, as they were some 150 years ago. Some sections – such as “Know Your Competition” – will resonate with those of us who compete for business with peers who once were fellow employees. Others, such as “See the Total Picture” will be valuable to those of us with responsibilities to national accounts and other nationwide programs. Other sections deal with discipline, the value of delegation, and the promotion of staff members – for good and ill – in ways that will ring true to professional security managers.

In the book’s Conclusion Kaltman offers the reader his take on “The Quintessential Grant” by encapsulating the lessons Grant applied throughout his military career:

Use the Planning Process to Set Priorities
Focus On the Contribution You Could Be Making
Be Persistent and Tenacious
Identify the Information You Need
Create a Thinking Machine
Surround Yourself with Good People
Remember That the Work Must Be Done By Others
Be Considerate and Fair to Your People
Make Allies of Those Who Do Not Report to You
Recognize That Success Is Temporary
Always Act Ethically
Trust Yourself To Make Good Decisions.

In his final chapter on Grant’s lackluster presidency Kaltman makes the case that Grant may have failed in political office precisely because he did not apply to political life the same skills he used as a military leader.

Perhaps there is nothing new under the sun. Perhaps it is no coincidence that Thucydides, Sun Tzu, and Shakespeare sound very contemporary to the thoughtful reader. Perhaps we have read all this before. Perhaps Kaltman’s gift to the reader is simply to have created a palatable delivery vehicle for common sense leadership methods. Perhaps the rest is up to us.
1,467 reviews19 followers
July 14, 2018
A person might think that the life of General (later President) Ulysses S. Grant is an unlikely place to find leadership lessons applicable to the modern age. That is what this book attempts to do.

Did you know that Grant was born Hiram Ulysses Grant? The Congressman who appointed him for West Point filled out the application for Ulysses S. Grant. When he tried to correct the error, the clerk at West Point said that the application could not be changed. Rule number one: try to keep bureaucrats out of your organization.

People need meaningful work. Interviews reveal more than resumes. You have to earn your stripes. Turn mistakes into training opportunities. It's not important who gets the credit. See for yourself what's happening. Committees study good ideas to death.

Know when to listen to your subordinates. Know when to disobey orders. There isn't only one right way. Know when not to hold a staff meeting. Ask the right questions. Sooner or later, everyone gets sick. Take responsibility for your actions. You can't succeed if they don't. How to pick the right person for the job. Know when something smells fishy. Never act in anger, regardless of the provocation. Unfortunately, President Grant was not able to put into practice the leadership lessons of General Grant.

This is a really good history/management book. Each leadership lesson is illustrated by an example from Grant's own memoirs. It is very much worth reading.
Profile Image for Erik.
Author 3 books8 followers
May 11, 2021
The title is fun but misleading. Grant didn't achieve so much winning through anything connected with either whiskey or cigars. In fact, both of the latter were harmful to Grant. Whiskey he managed to conquer through constant vigilance by himself, his wife Julia, and others close to him, to avoid drinking. And cigars wound up giving Grant throat cancer that killed him.

Fortunately, Kaltman's book is very little about smokes or drinks but mostly about about winning, how the lessons of Grant's victories on the battlefield in the Civil War can offer lessons to contemporary business managers to also win success.

And Kaltman makes a surprisingly good case that Grant's soldiering and generalship applies well to managing employees and fighting competitors today. Two hundred and fifty lessons include "The Folly of Swearing" (Grant avoided profanity), "Know Your Competition" (Grant got to know future Confederate adversaries when serving with them on the same side during the Mexican War) and "Everyone Is Mortal" (Grant was immune to the widespread overestimation of Robert E. Lee even in the North).

A good read for advice on business and as a quick, lively introduction to the life and military career of Grant as well.
Profile Image for Ethan West.
395 reviews8 followers
July 15, 2022
This was an interesting concept for a book. It was part biography and part one-off leadership lessons. I have definitely tucked some of those away for future use. Overall the lessons were good but I feel like the author was starting to grasp at straws towards the end. Plus, the title is misleading. I actually picked this book up because of the word cigar in the title. I was looking into books on cigars or cigar themed and this book had very little in the way of cigar info. Except for the short history of how Grant came to enjoy cigars more than pipes. Apparently, he was gifted a cigar at one time and that was all he had to smoke in battle. Because of news reports of him smoking the cigar during battle, he started receiving cigars as gifts, and, despite giving away as much as he could, he found himself with an overabundance of them. He started smoking them regularly afterward so as not to let them go to waste.
3 reviews
June 6, 2020
This book was recommended to me by a four star general over a decade ago, and I just finished reading it for the second time. It is a unique book on management using examples from Grant’s time in the military. It’s a relatively short read that I highly recommend. I am giving the book 4 stars instead of 5 for two reasons. The first is that a few of the lessons presented in the book appear to be contradictory. The second is that this is less of a book on Grant’s management style and more of a book of management lessons the author believes in, and he uses examples of Grant’s career to highlight. It’s as if the author wrote the lessons, and then scanned Grant’s papers for material in support of these lessons. Still, the book presents some valuable lessons, and is certainly worth reading—especially for those in positions of leadership.
Profile Image for Spencer.
38 reviews
April 7, 2024
The book has interesting snippets about Ulysses S Grant. It has good leadership lessons too. But they have rarely to do with each other.

Most lessons are genuinely helpful. Some are redundant. Some are a stretch to the stories they are attached to. It felt like two books stitched together.

Thankfully, it's a quick read. For those needing leadership tips, I'd recommend this book. But I'd prefer a version with just the tips. I believe they can find another, better book solely about Grant elsewhere.
Profile Image for Eric.
81 reviews
October 10, 2020
If you just read the leadership summary at the end of each section, you will walk away educated with sound leadership principles. This book is more. I gained insight into the challenges of the civil war. Through the eyes and pen of a good man, I learned of his worries, compassion, humility, commander-intrigue, and details of the battles and war. This was a short introduction to the life of Ulysses Grant, which will make me a better business leader.
Profile Image for James.
55 reviews2 followers
November 6, 2021
Quick, easily digestible, leadership nuggets based on General Grant’s experiences. Some were a stretch of interpretation but the single page format made this different from most leadership tomes.

I’ve never read that much about Grant before but after reading this I’m interested in reading his memoirs or a biography. He seems to be much more than the General, President, and (allegedly) a heavy drinker.
Profile Image for Gary.
Author 5 books2 followers
April 19, 2024
I enjoyed it. Very different way to look at and draw lessons from history. The bite-sized stories made it so easily readable--a literary version of munching on a bag of chips (but with a bit more nutrition). I do think it simplified things a little bit too much maybe, and sometimes felt cliche in the leadership advice, but it was a very worthwhile read.
36 reviews
October 11, 2019
Very interesting, entertaining and enlightening series of anecdotes. An easy read and yet thought provoking at the same time. It is easy to see why Grant was overlooked so often until Lincoln realized the gem he had.

3 reviews
June 24, 2019
Small short stories about Grant in his time at a civilian and soldier. All of which that can relate to anyone in their current life situation.
2 reviews
August 27, 2020
Great book, full of stories that range from humorous to sobering. Each one carrying great leadership lessons that anyone could learn from.
1 review
January 29, 2017
Ez read

Broken up page by page. I liked the lessons on each page would recommend good leadership thoughts and ideas. Will use them
Profile Image for J. S. Seebauer.
Author 2 books183 followers
December 29, 2007
This book is good for those who are history buffs and...

1. are in management / supervision -- It has tales of Grant's life and how they relate to being the best manager / supervisor.

2. enjoy a pick-up / put-down / start anywhere kind of book. Each tale is only a page or two long making it easy to start and stop quickly.
Profile Image for Vutha Um.
10 reviews
May 10, 2016
I thoroughly enjoyed this book and I highly recommend it. It's a great read for people in managerial position. It will either enhance your skills and/or teach you new skills to become a more efficient leader. This book will sharpen your mind and motivate you to be better than you are for the sake of your personal and business relationships.
Profile Image for Doug Naquin.
41 reviews1 follower
August 25, 2012
Companion book to a book on Robert E. Lee I read in 2008. 250 lessons on leadership taken from vignettes of Grant’s military career. Grant’s memoirs appear to have provided most of the material. Fast read over the Columbus Day weekend.
1 review
May 5, 2008
Given to me as award for being Honor Grad of MVOC. Woo-Hoo!

It's actually a pretty good book, with good lessons. Not something that I would have picked for myself, though.
Profile Image for Trekscribbler.
227 reviews10 followers
May 1, 2011
The quickest 300+ page book I've ever read! Great adaptation of the U.S. Grant biographical information applied to serious management methodology ... a masterpiece.
Profile Image for Backslash.
272 reviews1 follower
November 8, 2014
good management book. as usual it is mostly common sense but it delivers the content in a civil war context and each lesson is just a page so it is easy to pick up and put down.
6 reviews
March 7, 2014
This book does a good job of recounting Ulysses Grant's experiences and making it correlate with leadership skills. Makes sense of all examples well with the lesson.
Profile Image for Charis Branson.
33 reviews
July 9, 2015
A lot of the leadership lessons seemed like common sense, but I enjoyed learning so much about my favorite General. I think the authors perspective on Grant was very interesting and informative.
Profile Image for Cara.
9 reviews
May 18, 2012
Good for coffee table or office desk book
51 reviews
March 8, 2018
Very interesting history and good leadership lessons.
Displaying 1 - 27 of 27 reviews

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